Compendium of Organic Synthetic Methods
Compendium of Organic Synthetic Methods Volume 10 MICHAEL 6.SMITH DEPARTMENT OF CHEMISTRY THE UNIVERSITY OF CONNECTICUT STORRS CONNECTICUT
.
@WILEY-INTERSCIENCE A JOHN WILEY & SONS, INC., PUBLICATION
Cover illustration was adapted from “Disconnect By the Numbers: A Beginner’s Guide to Synthesis” by M. B. Smith. Journal of Chemical Education, 1990,67, 848-856.
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1098 7 6 5 4 3 2 1
CONTENTS PREFACE ABBREVIATIONS INDEX, MONOFUNCTIONAL COMPOUNDS INDEX, DIFUNCTIONAL COMPOUNDS INTRODUCTION 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16
PREPARATION OF ALKYNES PREPARATION OF ACID DERIVATIVES AND ANHYDRIDES PREPARATION OF ALCOHOLS PREPARATION OF ALDEHYDES PREPARATION OF ALKYLS, METHYLENES AND ARYLS PREPARATION OF AMIDES PREPARATION OF AMINES PREPARATION OF ESTERS PREPARATION OF ETHERS, EPOXIDES AND THIOETHERS PREPARATION OF HALIDES AND SULFONATES PREPARATION OF HYDRIDES PREPARATION OF KETONES PREPARATION OF NITRILES PREPARATION OF ALKENES PREPARATION OF OXIDES PREPARATION OF DIFUNCTIONAL COMPOUNDS
AUTHOR INDEX
vii ix xiii xiv xv 1 7 12 45 57 100 118 139 157 170 177 183 206 21 1 229 238 349
V
PREFACE Since the original volume in this series by Ian and Shuyen Harrison, the goal of the Compendium of Organic Synthetic Methods was to facilitate the search for functional group transformations in the original literature of Organic Chemistry. In Volume 2, difunctional compounds were added and this compilation was continued by Louis Hegedus and Leroy Wade for Volume 3 of the series. Wade became the author for Volume 4 and continued with Volume 5. I began editing the series with Volume 6, where I introduced an author index for the first time and added a new chapter (Chapter 15, Oxides). Volume 7 introduced Sections 378 (Oxides - Alkynes) through Section 390 (Oxides - Oxides). The Compendium is a handy desktop reference that will remain a valuable tool to the working Organic chemist, allowing a "quick check" of the literature. It also allows one to "browse" for new reactions and transformations that may be of interest. The body of Organic literature is very large and the Compendium is a focused and highly representative review of the literature and is offered in that context. Compendium of Organic Synthetic Methods, Volume 10 contains both functional group transformations and carbon-carbon bond forming reactions from the literature appearing in the years 1996, 1997 and 1998. The classification schemes used for volumes 6-9 have been continued. Difunctional compounds appear in Chapter 1-6. The experienced user of the Compendium will require no special instructions for the use of Volume 10. Author citations and the Author Index have been continued as in Volumes 6-9. Every effort has been made to keep the manuscript error free. Where there are errors, I take full responsibility. If there are questions or comments, the reader is encouraged to contact me directly at the address, phone, fax, or Email addresses given below. As I have throughout my writing career, I thank my wife Sarah and my son Steven who have shown unfailing patience and devotion during this work. I also thank Dr. Darla Henderson, the editor for this volume. Michael B. Smith Department of Chemistry University of Connecticut 55 N. Eagleville Road Storrs, Connecticut 06269-3060 Voice phone: (860)-486-2881 Fax: (860)-486-2981 Email:
[email protected] Storrs, Connecticut
vii
AB BREVIATIONS
Ac acac AIBN aq.
9
/EL-
9-BBN BER BINAP Bn Bz
AcetyI Acet ylacetonate uzo-bis-isobutyronitrile Aqueous
J
CH,
9-Borabicyclo[3.3. llnonylboryl 9-Borabicyclo[3.3. llnonane Borohydride exchange resin 2R,3S-2,2'-bis-(diphenyIphosphino)1,1'-binaphthyl benzyl benzoyl 0
$
BOC
t-Butoxycarbonyl
bPY (BiPY) Bu CAM CAN cat.
2,2'-Bipyridyl n-Butyl Carboxamidomethyl Ceric ammonium nitrate cycloCatalytic
Cbz Chirald COD COT CP CSA CTAB
OCH2Ph Carbobenzyloxy 2S,3R-(+)-4-dimcthylamino- 1,2-diphenyl-3-methylbutan-2-ol 1,5-CyclooctadienyI I ,3,5-cyclooctatrienyI Cyclopentadienyl Camphorsulfonic acid cetyltrimethylammonium bromide C, ,H,,NMe3+Br
CY (C-C,H,J "C DABCO dba DBE DBN DBU DCC DCE DDQ % de DEA
Cyclohexyl Temperature in Degrees Centigrade 1,4-Diazabicylco[2.2.2]octane dibenzylidene acetone 1,2-Dibromoethahe 1,S-Diazabicyclo[S .4.0]undec-7-ene I ,5-Diazabicyclo[4.3.O}non-5-ene 1,3-Dicyclohexylcarbodiimide 1,2-Dichloroethane 2,3-Dichloro-5,6-dicyano1,4-benzoquinone % Diasteromeric excess Diethy lamine
C-
OtBu
-CH,CH,CH,CH, (NH,),Ce(NO&
.il
BrCH,CH,Br
c-C~H,,-N=C=N-C-C,H~ 1 ClCH,CH,CI
WCH,CH,)2 ix
X
ABBREVIATIONS
DEAD Dibal-H Diphos (dppe) Diphos-4 (dppb) DMAP DMA DME
Diethy Iazodicarboxylate Diisobutylaluminum hydride 1,2-bis-(DiphenyIphosphino)ethane 1,4-bis-(Diphenylphosphino)butane 4-Dimethylaminopyridine Dimethy lacetamide Dimethoxyethane
EtO,C-N=NCO,Et (Me,CHCH2),A1H Ph,PCH,CH2PPh2 Ph2P(CH2)4PPh,
DMF dmP dpm dPPb dPPe dPPf dPPP dvb e YOee EE Et EDA EDTA FMN fod FP FVP h hv 1,5-HD HMPA HMPT iPr LICA (LlPCA) LDA LHMDS LTMP MABR MAD mCPBA Me MEM Mes MOM Ms MS MTM NAD NADP
N,N-Dimethylformamide H N(CH3)2 bis-[ 1,3-Di(p-methoxyphenyI)-1,3-propanedionato] dipivaloylmethanato 1,4-bis-(DiphenyIphosphino)butane Ph,P(CH,),PPh, 1,2-bis-(DiphenyIphosphino)ethane Ph,PCH2CH2PPh2 bis-(Dipheny1phosphino)ferrocene 1,3-bis-(DiphenyIphosphino)propane Ph,P(CH,),PPh, Divinylbenzene Electrolysis % Enantiomeric excess 1-Ethoxyethoxy EtO(Me)CHEthyl -CH,CH3 Ethylenediamine H2NCH2CHzNHZ Ethylenediaminetetraacetic acid Flavin mononucleotide tvis-(6,6,7,7,8,8,8)-Heptafluoro-2,2-dimethyl-3 $octanedionate Cyclopentadienyl-bis-carbonyliron Flash Vacuum Pyrolysis hour (hours) Irradiation with light l$Hexadienyl Hexamethylphosphoramide (Me2N),P=0 Hexamethylphosphorus triamide (Me2N)P Isopropyl -CH(CH3)2 Lithium cyclohexylisopropylamide Lithium diisopropylamide LiN(iPr), Lithium hexamethyl disilazide LiN(SiMe3)2 Lithium 2,2,6,6-tetramethylpiperidide Methylaluminum bis-(4-bromo-2,6-di-tert-butylphenoxide) bis-(2,6-di-t-butyl-4-methylphenoxy)methyl aluminum meta-Chloroperoxybenzoic acid Methyl -CH3 MeOCH2CH20CH2P-Methoxyethoxymethyl 2,4,6-tri-Me-C,H2 Mesityl MeOCH,Methoxymethyl Methanesulfonyl CHjSO2Molecular Sieves (3A or 4A) Methylthiomethyl CH3SCH2Nicotinamide adenine dinucleotide Sodium triphosphopyridine nucleotide
MeOCH,CH,OMe
B
ABBREVIATIONS
xi
Napth NBD NB S NCS NIS Ni(R) NMP Oxone
Naphthyl (C&d Norbornadiene N-Bromosuccinimide N-Chlorosuccinimide N-Iodosuccinimide Raney nickel N-Methyl-2-pyrrolidinone 2 KHSO,.KHSO4.K2S04
PCC PDC PEG
Polymeric backbone Pyridinium chlorochromate Pyridinium dichromate Polyethylene glycol
Ph PhH PhMe Phth pic
Phenyl Benzene Toluene Phthaloyl 2-Pyridinecarboxylate
Pip PMP Pr
Piperidino 4-methoxypheny l n-Propyl
PY quant. Red-A1 sBu sBuLi Siamyl TADDOL TASF TBAF TBDMS TBHP (t-BuOOH) t-Bu TEBA TEMPO TFA TFAA Tf (OTf) THF THP TMEDA TMG TMS TMP TPAP
Pyridine Quantitative yield [(MeOCH2CH20)2AIH2]Na CH,CH,CH(CH,) sec-Buty1 sec-Butyllithium CH3CH2CH(Li)CH3 Diisoamyl (CHACHCH(CH,)a,a,a1,a'-tetraaryl-4,5-dimethoxy1,3-dioxolane tris-(Diethy1amino)sulfonium difluorotrimethyl silicate Tetrabutylammonium fluoride n-Bu4N+Ft-BuMe,Si t-Butyldimethylsily 1 Me,COOH t-Butylhydroperoxide -C(CH,), tert-Butyl Bn(Et),N+ Triethylbenzylammonium Tetramethylpiperdinyloxy free radical Trifluoroacetic acid Trifluoroacetic anhydride Triflate Tetrahydrofuran Tetrahydropyran Me2NCH2CH2NMe2 Tetramethylethylenediamine 1,1,3,3-TetramethyIguanidine -Si(CH3), Trimethy lsilyl 2,2,6,6-Tetramethylpiperidine tetra-n-Propylammonium perruthenate
xii
To 1 Tr TRlS Ts(Tos) x c
ABBREVIATIONS
Tolyl Trityl Triisopropylphenylsulfonyl Tosyl = p-Toluenesulfonyl Chiral auxiliary
4-MeC6H,S0,
INDEX, MONOFUNCTIONAL COMPOUNDS Sections-heavy type Pages-light type
1Pg.
sed. csrboxylicacids
Alcohols,phenols Aldehydes Amides Ammes Kctones
30A 11 45A 40 60A 54 9OA 117 lO5A 138 18OA 203
B W s in the table
mcspond to scaions for which no additional cxamples were found in the literature
AlLyncs
;
Carboxylic acid derivatives
Alcohols. phmols
61 57
17 8 18
33
19
34
u)
35
8
6 3
R
8
32 12
12
Estm
36
Hydrides (RH) Kctones
Misccllaumus
65
80
51
10
38
11
5 12 5
25 9
n
10
10
106
139
Ul
68 63
139
94
118
108 141
109 145
123 157
39
54
69 64
40
55
70
41
56
32
33
42 34
44 39
82
97
51 52
52
65
111
98
127
153
168
177
158
130
161
116
152
178
178
U9
174
207
im
214
186
190
207
is7
175
180
192
217
231
203
190
160
218
204
218
190 205
208 219
194
in
102 117
73
88
103
59
74
89
104 119
134
149
179
198
209
60
75
90
105 120
135 169
150 165
180
195 210
71
53
54
72
97
113 113
114 115
131
153
132
163
175
133
231
220
236.
162
181
207 222
194
163
131
132
219
176
m
72
229
215
207
192
213
230
190
179
146
174
229
184 199
159 174 145
212 198 213
158 173
147
100 115
86
182
207
188
142 157 172
113
150
169
171
160
128
185
187
173
114
183
170
111
146
149
127
112
170
167
w
121
99 85 111
138
152
171
171
120
1% 212
183
140 96
83
166
157
107
81
103
72
29
102
108
Nitriles Alkmes
79
50
28
28 4
118
2 6 5 0 6 0 1 0 2
37
8 4
101
64
60 50
n
91
75
21
Ethas, epxoides Ialides. sulfmates
46
100
100
48
13
27 Amhes
47 45
76
182
155
156
163
175 176
182
199
194 209 223
209 227
225 237
xiii
INDEX, DIFUNCTIONAL COMPOUNDS Sections-heavy type Pages-light type Blanks in the table correspond to sections for which additional examples were found in the literature.
scctions-beavytype Pagcs-light typc
302 239
313
323
315 244
325 253
243
316
255
317
327 2 9
307 241
334
278
32.8 260
246
319
329 264
3to 246
330 266
378
341
xiv
322
280
344
332 380
341
351 291
302
346
353 293
359 304
348
355
349
356
382
383
281 337 278
341
357
345 282 282
331 311
342
326
245
24s
309 241
247
343
343
364
561)
312
323
366
370
373
362
367
371
374
384 344
385 345
376
377
INTRODUCTION Relationship between Volume 10 and Previous Volumes. Compendium of Organic Synthetic Methods, Volume 70 presents about 1200 examples of published reactions for the preparation of monofunctional compounds, up-dating the 11850 in Volumes 1-9. Volume 10 contains about 550 examples of reactions that prepare difunctional compounds with various functional groups. Reviews have long been a feature of this series, but Volume 10 adds only 13 pertinent reviews in the various sections. Chapters 1-14 continue as in Volumes 1-9, as does Chapter 15, introduced in Volume 6. Difunctional compounds appear in Chapter 16, as in Volumes 6-9. The sections on oxides as part of difunctional compounds, introduced in volume 7, continues in Chapter 16 of Volumes 8-10 with Sections 378 (Oxides-Alkynes)through Section 390 (Oxides-Oxides). Following Chapter 16 is a complete alphabetical listing of all authors (last name, initials). The authors for each citation appear below the reaction. The principle author is indicated by underlining (i.e., Kwon, T.W.; Smith, M.B.),as done previously in Volumes 7-9. Classification and Organization of Reactions Forming Monofunctional Compounds. Chemical transformations are classified according to the reacting functional group of the starting material and the functional group formed. Those reactions that give products with the same functional group form a chapter. The reactions in each chapter are further classified into sections on the basis of the functional group of the starting material. Within each section, reactions are loosely arranged in descending order of year cited (1998-1996), although an effort has been made to put similar reactions together when possible. Review articles are collected at the end of each appropriate section. The classification is unaffected by allylic, vinylic, or acetylenic unsaturation appearing in both starting material and product, or by increases or decreases in the length of carbon chains; for example, the reactions t-BuOH -+ t-BuCOOH, PhCH,OH -+ PhCOOH, and PhCH=CHCH20H -+ PhCH=CHCOOH would all be considered as preparations of carboxylic acids from alcohols. Conjugate reduction and alkylation of unsaturated ketones, aldehydes, esters, acids, and nitriles have been placed in Sections 74D and 74E (Alkyls from Alkenes), respectively. The terms hydrides, alkyls, and aryls classify compounds containing reacting hydrogens, alkyl groups, and aryl groups, respectively; for example, RCH2-H -+ RCH2COOH(carboxylic acids from hydrides), RMe + RCOOH (carboxylic acids from alkyls), RPh -+ RCOOH (carboxylic acids from aryls). Note the distinction between R2C0 -+ R2CH2(methylenes from ketones) and RCOR' -+ RH (hydrides from ketones). Alkylations involving additions across double bonds are found in Section 74 (alkyls, methylenes, and aryls from alkenes). xv
INTRODUCTION
xvi
The following examples illustrate the classification of some potentially confusing cases: RCH=CHCOOH+ RCH=CH, + ArH + ArH + RCHO + RCH=CHCHO + RCHO + R2CH2 + RCHZCOR + RCH=CH2 +
RCH=CH2 RCH=CHCOOH ArCOOH ArOAc RH RCH=CH, RCH3 R2CO RZCHCOR RCHPCH,
RBr+HC+CH -+
RC+CR
ROH + RCOOH + RCOOR RCH=CHCHO RCH=CHCN
RCH2CH,CH0 +
RCH2CH2CN
Hydrides from carboxylic acids Carboxylic acids from hydrides Carboxylic acids from hydrides Esters from hydrides Hydrides from aldehydes Hydrides from aldehydes Alkyls from aldehydes Ketones from methylenes Ketones from ketones Alkyls from alkenes (Hydrogenation of Alkenes) Acetylenes from halides; also acetylenes from acetylenes Esters from alcohols; also esters from carboxylic acids Alkyls from alkenes (Conjugate Reduction) Alkyls from alkenes (Conjugate Reduction)
How to Use the Book to Locate Examples of the Preparation of Protection of Monofunctional Compounds. Examples of the preparation of one functional group from another are found in the monofunctional index on p x, which lists the corresponding section and page. Sections that contain examples of the reactions of a functional group are found in the horizontal rows of this index. Section 1 gives examples of the reactions of acetylenes that form new acetylenes; Section 16 gives reactions of acetylenes that form carboxylic acids; and Section 31 gives reactions of acetylenes that form alcohols. Examples of alkylation, dealkylation, homologation, isomerization, and transposition are found in Sections 1, 17, 33, and so on, lying close to a diagonal of the index. These sections correspond to such topics as the preparation of acetylenes from acetylenes; carboxylic acids from carboxylic acids; and alcohols, thiols, and phenols from alcohols, thiols, and phenols. Alkylations that involve conjugate additions across a double bond are found in Section 74E (Alkyls, Methylenes, and Aryls from Al kenes). Examples of name reactions can be found by first considering the nature of the starting material and product. The Wittig reaction, for instance, is in Section 199 (Alkenes from Aldehydes) and Section 207 (Alkenes from Ketones). The aldol condensation can be found in the chapters on difunctional compounds in Section 324 (Alcohol, Thiol-Aldehyde) and in Section 330
INTRODUCTION
xvii
(Alcohol, Thiol-Ketone). Examples of the synthetically important alkene metathesis reaction are mostly found in Section 209 (Alkenes from Al kenes). Examples of the protection of acetylenes, carboxylic acids, alcohols, phenols, aldehydes, amides, amines, esters, ketones, and alkenes are also presented. Sections (designated with an A: 15A, 30A, etc.) are labeled "protecting group: reactions" and are located at the end of pertinent chapters. Some pairs of functional groups such as alcohol, ester; carboxylic acid, ester; amine, amide; and carboxylic acid, amide can be interconverted by simple reactions. When a member of these groups is the desired product or starting material, the other member should also be consulted in the text. The original literature must be used to determine the generality of reactions, although this is occasionally stated in the citation. This is only done in cases where such generality is stated clearly in the original citation. A reaction given in this book for a primary aliphatic substrate may also be applicable to tertiary or aromatic compounds. This book provides very limited experimental conditions or precautions and the reader is referred to the original literature before attempting a reaction. In no instance should a citation in this book be taken as a complete experimental procedure. Failure to refer to the original literature prior to beginning laboratory work could be hazardous. The original-papers usually yield a further set of references to previous work. Papers that appear after those publications can usually be found by consulting Chemical Abstracts and the Science Citation Index. Classification and Organization of Reactions Forming Difunctional Compounds. This chapter considers all possible difunctional compounds formed from the groups acetylene, carboxylic acid, alcohol, thiol, aldehyde, amide, amine, ester, ether, epoxide, thioether, halide, ketone, nitrile, and alkene. Reactions that form difunctional compounds are classified into sections on the basis of two functional groups in the product that are pertinent to the reaction. The relative positions of the groups do not affect the classification. Thus preparations of 1,2-amino-alcohols, 1,3-amino-alcohols,and 1,4-amino-alcohols are included in a single section (Section 326, AlcoholAmine). Difunctional compounds that have an oxide as the second group are found in the appropriate section (Sections 278 - 290). The nitroketone product of oxidation of a nitroalcohol is found in Section 386 (Ketone-Oxide). Conversion of an oxide (such as nitro or a sulfone moiety) to another functional group is generally found in the "Miscellaneous" section of the sections concerning monofunctional compounds. Conversion of a nitroalkane to an amine, for example, is found in Section 105 (Amines from Miscellaneous Compounds). The following examples illustrate applications of this classification system:
xviii
INTRODUCTION
Difunctional Product RCEC-CGCR RCH(0H)COOH RCH=CHOMe RCHF, RCH(Br)CH,F RCH(OAc)CH,OH RCH(0H)C02Me RCH=CHCH,CO,Me RCH=CHOAc RCH(OMe)CH2S02CH2CH20H RS02CH2CH20H
Section Title Acety lene-Acetylene Carboxylic acid-Alcohol Ether-Alkene Halide-Halide Halide-Halide Alcohol-Ester Alcohol-Ester Ester-Alkene Ester-Alkene Alcohol-Ether Alcohol-Oxide
How to Use the Book to Locate Examples of the Preparation of Difunctional Compounds. The difunctional index on p xi gives the section and page corresponding to each difunctional product. Thus Section 327 (Alcohol, Thiol-Ester) contains examples of the preparation of hydroxyesters; Section 323 (Alcohol, Thiol-Alcohol, Thiol) contains examples of the preparation of diols. Some preparations of alkene and acetylenic compounds from alkene and acetylenic starting materials can, in principle, be classified in either the monofunctional or difunctional sections; for example, the transformation RCH=CHBr -+ RCH=CHCOOH could be consider as preparing carboxylic acids from halides (Section 25, monofunctional compounds) or preparing a carboxylic acid-alkene (Section 322, difunctional compounds). The choice usually depends on the focus of the particular paper where this reaction was found. In such cases both sections should be consulted. Reactions applicable to both aldehyde and ketone starting materials are in many cases illustrated by an example that uses only one of them. Likewise, many citations for reactions found in the Aldehyde-X sections, will include examples that could be placed in the Ketone-X section. Again, the choice is dictated by the paper where the reaction was found. Many literature preparations of difunctional compounds are extensions of the methods applicable to monofunctional compounds. As an example, the reaction RCI -+ ROH might be used for the preparation of diols from an appropriate dichloro compound. Such methods are difficult to categorize and may be found in either the monofunctional or difunctional sections, depending on the focus of the original paper.' The user should bear in mind that the pairs of functional groups alcohol, ester; carboxylic acids, ester; amine, amide; and carboxylic acid, amide can be interconverted by simple reactions. Compounds of the type RCH(OAc)CH,OAc (ester-ester)would thus be of interest to anyone preparing the diol RCH(OH)CH,OH (alcohol-alcohol). Sources of Literature Citations. I thought it would be useful for a reader of this Compendium to see those journals that contain the most new syn-
INTRODUCTION
xix
thetic methodology). The accompanying graph shows that Tetrahedron Letters and Journal of Organic Chemistry account for roughly 50% of all the citations in Volume 10. This book was not edited to favor one journal, section or type of article over another. Undoubtedly, my own personal preferences are part of the selection, but I believe that this compilation is an accurate representation of new synthetic methods that appear in the literature for this period. Therefore, l believe the accompanying graph reflects those journals where new synthetic methodology is located. I should point out that the category "15 other journals" includes: Accts. Chem. Res.; Acta Chem. Scand.; Angew. Chem. Int. Ed. Engl.; Bull. Chim. SOC. Fr; Bull. Chim. SOC.Belg.; Bull. Chem. SOC.Jpn.; J. Chem. Res. (S); Can. J. Chem.; Heterocycles; J. Heterocyclic Chem.; J. Indian Chem. SOC.; Liebigs Ann. Chem.; Org. Prep. Proceed Int.; and, European J. Org. Chem. In addition, nine more journals were examined but no references were recorded.
Compendium, Volume 10
Compendium of Organic Synthetic Methods
Compendium of’Ovganic Synthetic Methods Micheal B. Smith Copyright 02002 by John Wiley & Sons, Inc
CHAPTER 1 PREPARATION OF ALKYNES
SECTION 1: ALKYNES FROM ALKYNES Ph
=
1. 1.5% HgCl2, BuLi 2. BnBr
* Ph\ph 65%
&h&;Wang, L. J. Org. Chem., I998, 63, 3497. Ph--C=C-I
PhSnBus,lO% CuI ,DMF
*
rt,6h Kanp.;Kim, W.-Y.; Jiao, X. Synthesis, 1998, 1252.
I
Ph--C=C-Ph 71%
+
Fiirstner.;Seidel, G. Angew. Chem Int. Ed., 1998, 37, 1734.
73% .-
1. t-Bu TeMe, hv
* PB -t-u 2. aq NaClO 3. heat Terao, J.; Kambe.N,; Sonoda, N. Tetrahedron Lett., 1998, 39, 5511. Ph-
Ph-
PhI , 1%PdC12(PPh3)2,2% CUI K2CO3/€€20,10%B u ~ N
*
Ph
92~88%
=
Ph
98% Bumasin. N.A,; Sukhomlinova,L.I.; Luzikova, E.V.; Tolstaya, T.P.; Belestskava. I.P, Tetrahedron Lett.. 1996. 37. 897.
Compendium of Organic Synthetic Methods, Vol 10
2
d
c3H7
Ph
*
THF . HMPA
Me
Makioka, Y .; Saiki, A.; Takaki,K.; Taniguchi, Y .; Kitamura, T.; Chem. Lett., 1997, 27.
II
5% Pd(PPh&, 10%CUCl DMF ,80"C, 12 h
=
Section 1
c3H7
89%
t
. . Nlshlhara.; Ikegashira, K.; s Hiyama, ; T. Chem. Lett., 1997, 1233.
B
cyclohexyl-CHO ,DCE , -78°C
*
72% (74% ee) Angel], R.M.; Barrett.;Braddock, D.C.; Swallow, S.; Vickery, B.D. Chem. Commun., 1997, 919.
PhI , Pd(OAc)z, PPh3 , aq MeCN Ph
Bu&HSOflt3 ,25"C, 1.5 h
t
(1
89%
3
Akynes from Amides
Section 6
Ph2IPh' BF4-, 0.2% Pd(0Ac)z
Ph-
NaHCO3 ,aq MeCN ,rt , 10 min
*
=
Ph
Ph
96% Kang. S.-KL; Lee, H.-W.; Jang, S.-B.; Ho, P.-S. Chem. Commun., 2996, 835. H C S H , [Pd(PPh3)dC12, NEt3
* PhCSPh CuI ,DMF ,60°C Pal, M.; Kundu. N.G,J. Chem SOC., Perkin Trans. 1, 2996, 449.
83%
PhI
SECTION 2: ALKYNES FROM ACID DERIVATIVES NO ADDITIONALEXAMPLES
SECTION 3: ALKYNES FROM ALCOHOLS AND THIOLS NO ADDITIONALEXAMPLES
SECTION 4: ALKYNES FROM ALDEHYDES
=
* Ph K2CO3, MeOH ,rt Miiller, S.; Liepold, B.; Roth, G.J.; Bestmann. H.J, SynLeff.,2996, 521. PhCHO
SECTION 5:
ALKYNES FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONALEXAMPLES
SECTION 6:
ALKYNES FROM AMIDES NO ADDITIONAL EXAMPLES
73%
4
Compendium of Organic Synthetic Methods, Vol 10
SECTION 7:
ALKYNES FROM AMINES
Section 10
NO ADDITIONAL EXAMPLES
SECTION 8:
ALKYNES FROM ESTERS
.Ph
Powell, N.A.; Rvchnovskv. S.D. Tetrahedron Lett., 1998, 39, 3103.
SECTION 9:
ALKYNES FROM ETHERS, EPOXIDES AND THIOETHERS NO ADDITIONAL EXAMPLES
SECTION 10:
ALKYNES FROM HALIDES AND SULFONATES
DCH0pc:: Me3SiC..CH, cat CuI
Br
a t Pd(PPh3)2C12,25"C
THF, NEt3,l h
MqSi Thorand, S.; Krause. N, J. Org. Chem., 1998, 63, 8551. H
MgBr
5% Pd(PPh3)4,22"C, 1h
. .
Neplshl.; Kotora, M.;
\ /
Xu,C. J. Org. Chem., 1997, 62, 8957.
92%
Section 12
Alkynes from Ketones
5
* PhXS-Ph ,P d d d b a ) ~THF , Ph--€=C-SnBus Shirakawa. E.; Yoshida, H.; Takaya, H. Tetrahedron Lett., 1997,38, 3759. Ph-I
93%
Snvdes. J . K, ; Bakstad, E. Acta Chem. Scad. B, 1996,50,446.
SECTION 11:
ALKYNES FROM HYDRIDES
en
For examples of the reaction RC=CH -+ RC=C-C=CR1, see section 300 (Alkyne-Alkyne).
P
i-Pr3SiC-=CH, AIBN MeCN ,reflux
*
Xiang, J.; Jiang, W.; EudsJL Tetrahedron Lett., Z997,38, 6635.
SECTION 12:
50%
ALKYNES FROM KETONES 0
ji
1. EiO’
\
OEt
, LHMDS , -78°C -+ rt e
2.2 eq BuLi , -60°C -+ rt
hP-P
Ph Ph 95% Mouriks, V.; Waschbiisch, R.; Carran, J.; Savignac, P. Synthesis, Z998,271. LDA , THF , -78°C
+
B V C f l 1 1
OTf 80%
Brummond.;Gesenberg, K.D.; Kent, J.L.; Kerekes, A.D. Tetrahedron Lett., 1998,39, 8613.
6
Compendium of Organic Synthetic Methods, Vol10
SECTION 13:
ALKYNES FROM NITRILES
Section 15A
NO ADDITIONAL EXAMPLES
SECTION 14:
ALKYNES FROM ALKENES NO ADDITIONAL EXAMPLES
SECTION 15:
ALKYNES FROM MISCELLANEOUS COMPOUNDS NO ADDITIONAL EXAMPLES
SECTION MA:
PROTECTION OF ALKYNES
NO ADDITIONAL EXAMPLES
Compendium of’Ovganic Synthetic Methods Micheal B. Smith Copyright 02002 by John Wiley & Sons, Inc
CHAPTER 2 PREPARATION OF ACID DERIVATIVES AND ANHYDRIDES
SECTION 16:
ACID DERIVATIVES FROM ALKYNES NO ADDITIONAL EXAMPLES
SECTION 17:
ACID DERIVATIVES FROM ACID DERIVATIVES
PhKcl
NaHCO3 ,MeCN , ultrasound
0
Hu, Y.;
*
45°C
phYolfph 0
98%
J.-X; Li, S . Synth. Commun., Z997, 27, 243.
SECTION 18:
0
ACID DERIVATIVES FROM ALCOHOLS AND THIOLS H ~ I Ocro3 ~ , , ooc
PhO -H
t
PhO C 0 2 H 96%
Zhao. M.; Li, J.; Song, Z.; Desmond, R.; Tschaen, D.M.; Grabowski, E.J.J.; Reider, P.J. Tetrahedron Lett., 1998, 39, 5323.
SECTION 19: ACID DERIVATIVES FROM ALDEHYDES PhCHO
Oxone, aq acetone, 25"C, 1 h
\nlebb.; Ruszkay, S.J. Tetrahedron, 1998, 54, 401.
t
PhCOOH
71%
Compendium of Organic Synthetic Methods, Vol 10
8
H202, aq HCl, MeOH
PhCHO
-
PhCO2hk
Section 23
95%
also works with acetals Takeda, T.; Watanabe, H.; Kitahara, T. SynLett., 1997, 1149.
ACID DERIVATIVES FROM ALKYLS, METHYLENES AND ARYLS
SECTION 20:
mesoporous chromosilicate (Cr-MCM-41) t-BuOOH ,120 h 45%
forms ketones from other arenes Das, T.K.; Chaudhari, K.; Nandanan, E.; Chandwadkar,A.J.H.; Sudalai, A.; Ravidranathan, T Sivasanker, S. Tetrahedron Lett., 1997, 38, 3631. REVIEW: "Exploitation of Synthetic Reactions via C-H Bond Activation by Transition Metal Catalysts. Carboxylation and Aminomethylation of Alkanes or Arenes." Takaki, K.; Tankguchi, Y . SynLett., 1996, 591.
m;
SECTION 21: ACID DERIVATIVES FROM AMIDES NO ADDITIONAL EXAMPLES
SECTION 22: ACID DERIVATIVES FROM AMINES NO ADDITIONAL EXAMPLES
SECTION 23: ACID DERIVATIVES FROM ESTERS NO ADDITIONAL EXAMPLES Other reactions useful for the hydrolysis of esters may be found in Section 30A (Protection of Carboxylic Acids).
Acids from Ketones
Section 27
SECTION 24:
-
9
ACID DERIVATIVES FROM ETHERS, EPOXIDES AND THIOETHERS NO ADDITIONALEXAMPLES
SECTION 25:
ACID DERIVATIVES FROM HALIDES AND SULFONATES NdV02, AcOH ,DMSO ,35"C
*
80%
Br Ph Matt, C.; Wagner, A.; Mioskowski. C, J. Org. Chem., 1997, 62, 234.
10% PdC12(PPh&. C02 O T f e- ,DMF ,20°C Iutand.;NCgri, S. SynLett., 1997, 719. P
h
t
P
h
e
C
e
e- ,0.1 BwxNBF4-DMF -lO°C, 20% NiBr2-bpy
Kamekawa, H.; Kudoh, H.; Senboku, H.; ll&.&JL
73% Chem. Lett., 1997, 917.
SECTION 26: ACID DERIVATIVES FROM HYDFUDES NO ADDITIONAL EXAMPLES
SECTION 27: ACID DERIVATIVES FROM KETONES
1.1 eq Tl(NOd3 r t , 2 4 h ,CH2C12
&*1111111C02H
-H
H ;-
Silva Jr., L.F. J. Org. Chem., 1998, 63, 1716.
93%
O
2
H
Compendium of Organic Synthetic Methods, Vol 10
10
A
Section 30
1. LiOCl , Chlorox ,EtOH
* PhC02H 95% 2. H30' Ph ; Benbrook, D.M: Madler, M.M.; Klucik, J.; Soell, P.S.; Brown, C.W.; Liu, S.; Birckbichler, P.J.; Nelson, E.C. Org. Prep. Proceed. Int., 1998, 30, 230.
I 87% Ferraz.; Silva Jr., L.F. Tetrahedron Lett., 1997, 38, 1899. t-Bu
SECTION 28: ACID DERIVATIVES FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION 29: ACID DERIVATIVES FROM ALKENES
F
Q = [(CgH17)3NMeJC Antonelli, E.; D'Aloisio, R.; Gambaro, M.; Fiorani, T.; k#wdhJ2 J. Org. Chem., 1998, 63, 7190.
B'w
KMn04/NaI04, sand, H20 . r
B.--C02H
79%
Juang, B.; Gupton, J.T.; Hansen. K.C,;Idoux, J.P. Synrh. Commun., 1996, 26, 165.
SECTION 30:
ACID DERIVATIVES FROM MISCELLANEOUS COMPOUNDS NO ADDITIONAL EXAMPLES
Section 30A
SECTION 30A:
Protection of Alcohols
11
PROTECTION OF CARBOXYLIC ACID DERIVATIVES
Other reactions useful for the protection of carboxylic acids are included in Section 107 (Esters from carboxylic Acids and Acid Halides) and Section 23 (Carboxylic Acids from Esters).
A o d
S-Sn02, PhOMe , toluene
Ph
heat, 7h
PhCOOH
+
82%
Chavan.;Zubaidha, P.K.; Dantale, S.W.; Keshavaraja, A.; Ramaswamy, A.V.; Ravindranathan, T. Tetrahedron Lett., 1996, 37, 237.
1. TeMaBH4, DMF ,80"C
pbK0-cc13
0 2.2M HCl Blay, G.; Cardona, L.; Garcia, B.; Garcia, C.L.;
)r
PhCOOH
Synth. Commun., 1998, 28, 1405
Compendium of’Ovganic Synthetic Methods Micheal B. Smith Copyright 02002 by John Wiley & Sons, Inc
CHAPTER 3 PREPARATION OF ALCOHOLS
NO ADDITIONAL EXAMPLES
SECTION 31: ALCOHOLS AND THIOLS FROM ALKYNES NO ADDITIONAL EXAMPLES
SECTION 32:
ALCOHOLS AND THIOLS FROM ACID DERIVATIVES
BOP = benzotriazol- 1-yloxytris(dimethylamino)phosphonium hexatluorophosphate Tetrahedron Lett., Z998, 39, 3319.
)o-
SECTION 33:
ALCOHOLS AND THIOLS FROM ALCOHOL AND THIOLS 1. ClCH2S02Cl. Py ,3h , 0°C +i~ 2. 3 CsOAc ,0.5 18-crown-6 PhH ,reflux, 5d
1111l1111,
$
3. base
*
)alNa
H 6 Ho Shimizu. T,; Hiranuma, S.; Nakata. T, Tetrahedron Lett., 1996, 37, 6145. OH
96~88%
1. Tf20 2. NaST(P5), Pd(PPh3)4
Amould.;Didelot, M.; Cadilhac, C.; Pasquet, M.J. Tetrahedron Lett., 1996, 37,4523.
Section 34A
Reduction of Aldehydes
13
SECTION 34: ALCOHOLS AND THIOLS FROM ALDEHYDES The following reaction types are included in this section: A. Reductions of Aldehydes to Alcohols B. Alkylation of Aldehydes, forming Alcohols. Coupling of Aldehydes to form Diols is found in Section 323 (Alcohol-Alcohol).
SECTION 34A:
REDUCTIONS OF ALDEHYDES TO ALCOHOLS IInClflu3SnHlTHFJ
* PhCHzOH -78°C + rt Miyai, T.; Inoue, K.; Yaw&, M.; Shibata, I.; Baba. A. Tetrahedron Lett., 1998,39, 1929. PhCHO
FeC13Znf DMFEI20.1 h
PhCHO
PhCHzOH
w
81%
also reduces ketones Sadavaarte, V.S.; Swami, S.S.; Desai. D.G,Synth. Commun., 1998,28, 1139.
m
C
H
O
1.NaBHflhCOOH. diglyme 2. (HOCHgH20),,--H
diglyme
90%
these conditions are selective for aldehydes B l a n t o n . S y n t h . Commun., 1997,27, 2093. PhCHO
PMHS ,ZnCI;?, 1 d
w
PhCH20H
PMHS = polymethylhydrosiloxane
Chandrasekhar.; Reddy, Y.R.; Tamarao, C. Synth. Commun., 1997,27, 2251.
a CHO
i-BuzAlOEt , ether, 0°C , 3 h
*
MOH
Cha.;Kwon, 0.0.;Kwon, S.Y. Org. Prep. Proceed. Int., 1996,28,355.
72%
Compendium of Organic Synthetic Methods, Vol 10
14
Section 34B
ALKYLATION OF ALDEHYDES, FORMING ALCOHOLS
SECTION 34B:
ASYMMETRIC ALKYLATIONS EtZZn ,cat chiral binaphthol
PhCHO
95% (>99% ee) J. Org. Chem., 1998, 63, 1364.
Huang, W.-S.; Hu, Q.-S.;
EtzZn , toluene
PhCHO
cat ferrocene carboxaldehyde 94% (91% ee,R)
a. S.-i.; Kato, H. SynLett., 1998, 727.
EtzZn, toluene, 0°C , 10 h
C3H7--CHO
*
C $ A o H
10% chiral amino alcohol
Et
L
88% (82% ee ,R) Cho. B.T,; Chun, Y.S. Tetrahedron Asymmetry, 1998, 9, 1489. EtzZn ,hexane, 0°C , 1 d
PhCHO M
e
O
A N L
srrr/
O
t
Ph
OMe
99% (91% ee)
H
Shi.;Satoh, Y.; Masaki, Y. J. Chem. Soc., Perkin Trans. I , 1998, 2547. PhCHO
EtzZn , THF
5% chid phosphine oxide
*I/ ph
quant (82% ee) Legrand, 0.;Brunel, J.-M.; Buono, G. Tetrahedron LRtt., 1998, 39, 9419. PhCHO
Me&, 14% TiF4, THF
OH -
80% (80% ee) chiral diol Ph Tetrahedron Lett., 1998, 39, 9593. Pagenkopf, B.L.; Qfr&a&U
- n
15
Alkylation of Aldehydes
Section 34B
1. Et2Zn , chiral biaryl catalyst
PhCHO
2. H2O quant (% er 1 9 ) Breuning, M. Tetrahedron Asymmetry, 1998, 9, 667.
;-
PhCHO
1
ZnEt2,3% chiral ferrocenyl catalyst
*
To1 ,rt
Ph
J. Org. Chem., 1997, 62, 444.
Et
88%(90%ee)
L +y-cH2cHrH,
Dosa, P.I.; Ruble, J.C.;
THF , -30°C
PhCHO
Ph
62% (82% ee , R)
Sugimoto, K.; Aoyagi, S.;
BZ
.
*L *L J. Org. Chem., 1997, 62, 2322.
EtzZn , -23"C, hexane
PhCHO
titanate complex
Qiu, J.; Guo, C.;
Ph
u Org. . Chem., 1997, 62, 2665.
99% (94% ee)
1. AlEt3, S-Hg-BLNOL PhCHO
quant (96% ee , S) Ph A.S.C.; Zhang, F.-y.; Yip, C.-W. J. Am, Chem. Soc., 1997, 119, 4080.
PhCHO
2. H+
1 . 3 eq EtzZn, toluene , 0°C , 1h S-BINOLmi(Oi-Pr)4
*
2. H+ Mori, M.; Nakai. T, Tetrahedron Lett., 1997, 38, 6233. SnBq
PhCHO
Yu. C.-&;
5% S-BINOL-Ti(Oi-Pr)4
PhI
t
>98% (84% ee ,S)
4L Ph
E
83% (93 ee)
Cho, H . 4 . ; Yoon, S.-K.; Jung, W.-H. SynLett., 1997, 889.
16
PhCHO
Compendiumof Organic Synthetic Methods, Vol 10
Section 34B
1.5% ferrocenyl catalyst, Et2Zn toluene ,O°C * 2. workup 83% (93% ee ,R )
Bolm.;Fernhdez, K.M.; Seger, A.; Raabe, G. SynLett., 1997, 1051. EtzZn, CHzCl2,O"C , 8 h
PhCHO
S-BINOL-Ti(Oi-Pr)4
*I/ Ph
L
quant (91.9% ee) Zhang, F.-Y.; u n -.C.-W.; Cao, R.; C t u n A S C Tetrahedron Asymmetry, 1997, 8, 585.
-
PhCHO
Et2Zn ,toluene-heme , 18 h
-
Ph
99% (89% ee ,S) Genov, M.; Dimitrov.,;Ivanova, V. Tetrahedron Asymmetry, 1997, 8, 3703.
Ph
(yf
(C5H11)2Zn ,Ti(Oi-Pr)4, 16 h
CHO
5%
,-45°C + -20°C
-
dC
Ph
"" NHTf 87% (85% ee) Vettel, S.; Lutz, C.; Diefenbach, A.; Haderlein, G.; Hammerschmidt, S.; Kiihling, K.; Mofid, M.-R.; Zimmerman, T.; I@dld& Tetrahedron Asymmetry, 1997, 8, 779.
Et2Zn ,hexane-toluene
Me Nakano, H.; Kumagai, N.;Matsuzaki, H.; Kubato, C.; Tetrahedron Asymmetry, 1997, 8, 1391.
co2i-pr PhCHO , toluene, 40 h COzi-Pr
-40°C
Zhang, L.C.; Sakurai, H.; Kira. M, Chem. Lett., 1997, 129.
73% (60%ee ,S)
Section 34B
17
Alkylation of Aldehydes
SnBu3
C7H sCHO
,CH2C12,22"C
Chid catalyst, ZnI2,18 h 68% (23% ee) Coi, P.G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi. A. Tetrahedron Lett., 1997, 38, 145. PhCHO
L Hs2b Et2Zn ,0°C ,7h
Ph
Y Nakano, H.; Iwasa, K.;
PhCHO
Ph
68% (94% ee , S)
Heterocycles, 1997, 46, 267.
-
EtzZn ,Ti(Oi-Pr14 ,bis-amine ligand hexane ,-23°C
L
Ph
98% (99% ee , S) Guo, C.; Qiu, J.; Zhane. X,; Verdugo, D.; Larter, M.L.; Christie, R.; Kenney, P.; Walsh. P.J, Tetrahedron, 1997, 53, 4145. SnBu3
PhCHO
4L
5% S-BINAPwAgOTf Ph Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto. H, J. Am. Chem. Soc., 1996, I I 8 , 4723.
x PhCHO
88% (96% ee ,5')
Ce- Bu
-1OO"C, ether
p * P h A B u
66% (66%ee)
m V e s . N.; Pease, J.E.; Bowden, M.C.; Brown, S.M. Tetrahedron Lett., 1996, 37, 2675. MQ *Ph H + - y 0 BuzN S--( , 6h
PhCHO
quant (>99% ee , S) Et Jim M.-L; Ahn, S.-J.; Lee, K . 3 . Tetrahedron Lett., 1996, 37, 8767. 2 eq Et2Zn ,hexane ,0 + 20°C
18
Compendium of Organic Synthetic Methods, Vol 10
Section 34B
, iPrSSiMe3 , CH2C12, -20°C
1. Bu3Sn-
PhCHO
.c
0 .Oil%
91% (97% ee)
0 TiOiPr
2. TBAF Yu. C.-M.; Choi, H.-S.; Jung, W.-H; Lee, S.S. Tetrahedron Lett., 1996, 37, 7095. PhCHO
l.ZnEt2, 5% S-hcc
*L
80% (94:6 S:R)
2. H30+
hcc = hyperbranched chiral catalysts
Bolm.;Demen, N.; Seger, A. Synktt., 1996, 387. PhCHO
4/
Et2Zn
aRy ,NOH
Ph
65% (47% ee ,R)
Ph
de Parrodi, C.A.; J&&jJ. ;Quintero-Cort&, L.; Amador, P. Tetrahedron Asymmetry, 1996, 7, 1915.
*I/
Prasad, K.R.K.; Joshi. N.N. Tetrahedron Asymmetry, 1996, 7, 1957.
PhCHO
EtZZn , Ti(Oi-Pr),
rs:em(oMeh
>98% (>98% ee , S)
ph
Ph Hulst, R.; Heres, H.; Fitzpatrick, K.; Pepper, N.C.M.W.; Kellogg, R.M. Tetrahedron Asymmetry, 1996, 7, 2755. PhCHO
binaphthyl dicarboxamide
.r
QH
air, ZnBu2 Ph Kitajima, H.; Ito, K.; Katsuki. T, Chem. Lett., 1996, 343.
80% (99% ee ,R)
Section 34B
ether, -98°C
PhCHO
hves.
PhCHO
19
Akylation of Aldehydes
66% (83% ee)
x;Pease, J.E. Tetrahedron Lett., 1996,37, 5821.
1.2 eq Et2Zn ,2.5 eq chiral diamine disulfide toluene, 0°C
*
2.1M HC1 Bibson. C.L,Chem. Commun., 1996,645. 1.25 eq Et2Zn , rt PhCHO
76% (87% ee ,R )
+ L Ph
l%
97% (98% ee ,S)
Se)z
*L
Wirth.; Kulicke, K.J.; Fragale, G. Helv. Chim. Acta, 1996, 79, 1957. 1.
SiMe3
,Ti(IV) complex
PhCHO CH2C12, MeCN
Ph
2.TBAF,THF
85% (80% ee) Gauthier Jr., D.R.; Carreira. E.M. Angew. Chem. Int. Ed., 1996,35, 2363.
NON-ASYMMETRIC ALKYLATIONS
PhCHO
*L
CF~CHZOH, THF , 6O"C, 3-5 h
Ph
82%
Asao, N.; Abe, N.; Tan, Z.;
SynLett., 1998,377.
+d \+ $
Compendium of Organic Synthetic Methods, Vol 10
20
CHo
-SnBu3
BH3*THF, 2 eq TFAA tartrate, -78"C, 10h
*
Me
(93 Marshall. J.A,; Palovich, M.R. J. Org. Chem., 1998,63, 4381.
i-RCHO,In,Hfl-
Section 34B
7) 70%
Br ;-
PhCHO
(65 35) 52% Bennett, G.D.; Isaac, M.B.; Chhatriwalla, A. J. Org. Chem, 1998,63, 1836
wBr ,In DMF ,0°C
*
>95% (65:35 syn:anfi) Ph+
Llovd-Jones. G.C. ; Russell, T. SynLeff., 1998,903.
Bra phm
Yi, X.-H.; Haberman, J.X.; b.C.-J,Synth. Commun., 1998,28, 2999. PhCHO , Sb* , B u m r
= HO
51% (92:8 erythro:threo) Jim, Q.-H.; Ren, P.-D.; Li, Y . 4 . ; Yao. Z.-P,Synth. Commun., 1998,28, 4151.
Ph
21
Alkylation of Aldehydes
Section 34B
10%Sn(OTf)z, CHzClz ,rt , 6 h
Ph
Ty:
Nokami. J.; Yoshizane, K.; Matsuura, H.; Sumida, S.-i. J. A m Chem.SOC.,2998, 120, 6609
1
-
Ph
Ph
h i , T.; Miura, T.; Maruoka, K. J. Am. Chem. SOC.,1998, 120, 10790.
Ellis, W.W.; Odenkirk, W.; EbwkhJL Chem. Commun., 1998, 1311.
PhCHO
PhB(0H)z , Rh(acac)dppf
Sakai, M.; Ueda, M.;
aq DME
*
92%
P h PhI Angew. Chem. Int. Ed., 1998, 37, 3279.
c1 SmIz, "HI-HMPA HO OHC 97% Matsuda. F,; Sakai, T.; Okada, N.; Miyashita, M. Tetrahedron Lett., 2998, 39, 863
22
Compendium of Organic Synthetic Methods, Vol 10
Section 34B
,SnC12, heptane , H20
PhCHO
PdCl2[PPh2(3-SOfla)Phl, 35"C, 7 h 98%
Okano.; Kiji, J.; h i , T. Chem. Lett., 1998, 5 . m
C
H
0
BEt3, Dh4F , B u m
e- , Pt-Cu
OH
77%
(Ihoi.; Youm, J.S.; Cho, C . 4 . ; Czae, M.-Z.; Hwang, B.K.; Kim-LS,
Tetrahedron Lett., 1998, 39, 4835.
&SnBq PhCHO
, 2 % Yb(OTf)3
MeCN , PhCO2H, rt , 1 5 min 89% Aspinall, H.C.; Gr.sves. N.; McIver, E.G. Tetrahedron Lett., 1998, 39, 9283, VCl4, EtZZn ,THF O0C,5h IS$taoka.;Makihira, I.; Utsunomiya, M.; PhCHO
L
JEt P
97%
*?-I: J. Org. Chem., 1997, 62, 8540. Ph
1. BuqnLi, -85°C + -40°C
I &OMS
2. PhCH2CH2CHO. -85°C. 3 h
Bu HiimhL; Kaneko, T.; Fujiwra, R.; Oku, A. J. Org. Chem., 1997, 62, 8966. PhCHO
-
Ge(CH2CH=CH2)4, MeN&-Hfl
10%Sc(OTf)3 Ph Akivama.;Iwai, J. Tetrahedron Lett., 1997, 38, 853.
94%
Section 34B
23
Akylation of Aldehydes
/C02Me
Ph
83% (1:l anti:syn)
panek.;Liu, P. Tetrahedron Lett., 1997, 38, 5127. SdZ
C7Hy,--CHO
a,
*
THP, 15 min C7H15 Hamann-Gaudinet, B.; Namv. J.-L.: Kagan. H.B, Tetrahedron Lett., 1997, 38,6585.
mBr
1. Mg-BiC13 , aq THF , 1 h
75%
2. ph-CHO
Wada.;Fukuma, T.; Morioka, M.; Takahashi, T.; Miyoshi, N.
84%
Tetrahedron Lett., 1997, 38, 8045. PhCHO
99%
B u 3 S n W
20%I d 3 , MeCN , 0°C bH Miyai, T.; Inoue, K.; Yasuda, M.; Baba. A,SynLett., 1997, 699.
PhCHO
&Br
*
Ph
Pb ,THF/H20/NH4Cl Zhou, J.-Y.; Jia, Y.; Sung, G.-F.; Yu. S.-LSynth. Commun., 1997, 27, 1899. PhCHO , BuflBr ,DMF BiC13, NaBH4,5OoC
kX.
86%(erythro only) P.-D.; Shao, D.; Dong, T.-W. Synth. Commun., 1997, 27, 2569.
99%
24
,Sb*,rt,6h
-Br
PhCHO
h
Section 34B
Compendium of Organic Synthetic Methods, Vol 10
*
91%
DMF ,H20 Ph P.-D.; Jin, Q.-H.; Yao, Z.P. Synth. Commun., 1997,27, 2761. m
)
4
S
n
L
,0.1 Sc(OTf), ,H20
PhCHO
* Ph 0.2 SDS-surfXtant, rt m a y a s h i . S,; Wakabayashi, T.; Oyamada, H. Chem Lett., 1997,831.
84%
2% [Rh(cod)(MeCN)2lBF4,PhSnMe3
85%
PhCHO
hP' THF ,6O"C Ph Moro, M.; Inoue, Y. Chem. Commun.,1997, 1621.
u;
1. t-Bu2Zn ,THF , -78°C , 2 h -
PhLi
YH
A
*
2.0.5 PhCHO , -78°C + rt Kondo. Y.; Fujinami, M.; Uchiyama, M.; Sakamoto. T, J. Chem. SOC.,Perkin Trans. I , 1997,799. PhCHO
P
mcl , 1.5 eq SnC12,3 eq KI
70%
Ph
92%
H20,35"C, 15 h Ph Houllemare, D.; Outurquin, F.; Paulmier. C. J. Chem. Soc., Perkin Trans. I, 1997,1629.
*
PhCHO aq THF ,Nafion-SC
91%
Ph
m.; Nagayama, S. J. Org. Chem., 1996,61, 2256. SnBus
PhCHO
SnC12, MeCN ,25"C, 2h Riguet, E.; Klement, I.; Reddy, Ch.K.; Cahiez. G.: Knochel. P. Tetrahedron Lett., 1996,37, 5865. PhCHO
Br-
quant. OH
,Mn ,cat PbC12
98% cat Me3SiC1, THF ,25"C, 30 min Takai. K,; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett., 1996,37, 7049.
Section 34B
25
Alkylation of Aldehydes
Phb
O
H
28) 85% Bbalka. G.W.; Narayana, C.; Reddy, N.K. Tetrahedron Lett., 1996,37,2181. Me3SiPhCHO
, MeNO2
2% Sc(OTf)3 ,14h
-
79%
Ph
(0%with no Sc(OTQ3 after 48 h) Agguwal- \LIc; Vennall, G.P. Tetrahedron Lett., 1996,37,3745.
PhCHO
SnI2, TBAI
OH
-
DMI, rt, 7 h
*
Ph
DMI = 1,3dimethyl-2-imidazolidinone ;-
PhCHO
13) 88%
(87
Kishida, M.; Kurusu, Y . Tetrahedron Lett., 1996,37,7103. Br
80% (1:1 anti:syn)
Sn , InC13, H 2 0 , 1 5 h
Li, X.-R.;Loh. T.-P, Tetrahedron Asymmetry, 1996,7,1535.
-0,
r
/OE'
0
OEt
PhCHO ,EtzZn, THF Pdddba)3-€HC13, PPh3
OH
Kmg. S.-K.; Kim, D.-Y.; Hong, R.-K.; Ho, P.-S. Synth. Commun., 1996,26, 1493. wCHO Ph
SiMe3
-
&
5% HN(S02F)2, CHzClz Ph 0°C , 5 min Kaur, G.; Manju, K.; Trehan. S, Chem. Commun., 1996,581.
75%
89%
26
Compendiumof Organic Synthetic Methods, Vol 10
Section 35
Nd Ogawa, Y.; Mori, M.; Saiga, A.; Takapi, K,Chem. Lett., 1996, 1069.
more C2 adduct with Nal3r
Righi.;DAchille, R.;
$’
F;-
1. Mn* 2. PhCHO
(>99:1C3:C2) Tetrahedron Lett., 1996, 37, 6893.
* HO
Mn* = Mn-graphite
” % , , , , ,
-t
H
Ph
(4159 threo:erythro) Brunner, H. Tetrahedron Lett., 1996, 37, 7009.
SECTION 35:
O
q
Ph 65%
ALCOHOLS AND THIOLS FROM ALKYLS, METHYLENES AND ARYLS
NO examples of the reaction R
R ~-+ ROH ( R I = d y l , ary~,etc.) occur in the literature. For reactions of the type RH + ROH (R = alkyl or aryl) see Section 41 (Alcohols and Phenols from Hydrides).
Section 37
27
Alcohols from Amines
(26 1) 18% 39% ee Hamada, T.; Me, R.; Mihara, J.; Hamachi, K.; Katsuki. T, Tetrahedron, 1998, 54, 10017.
Smitrovich, J.H.; Woerpel. K,A,J. Org. Chem., 2996, 61, 6044. 1. C- , TFNCHzC12
*
72%
2. NEt3 Fujimoto, K.; Toduda, Y.; Maekawa,H.; Matsubara, Y.; Mizuno, T.; Tetrahedron, 1996, 52, 3889.
SECTION 36: ALCOHOLS AND THIOLS FROM AMIDES
Mvers.;Yang, B.H.; Kopecky, D.J. Tetrahedron Lett. 2996, 37, 3623. SECTION 37: ALCOHOLS AND THIOLS FROM AMINES
x/
Ph
SO2Cl
1.
S0,CI
,NEt3 ,CH2C12 b
2. KN02, 18-C-6,DMF , 2O"C, 1 h
* QH -
-
Ph
70% (40% ee) Sbrbye, K.; Tautermann, C.; Carlsen, P.; Fiksdahl. A, Tetrahedron Asymmetry, 1998, 9,681
Compendium of Organic Synthetic Methods, Vol 10
28
Section 39
SECTION 38: ALCOHOLS AND THIOLS FROM ESTERS 1. dodecanethiol , air,light 2.PPh3
Ph
Ph
OH
72%
Barton.; Gkro, S.D.; Holliday, P.; Quiclet-Sire, B.; Zard, S.Z. Tetrahedron, 1998, 54, 6751.
H2 , R~(acac)3,NEt3 ,FIPA
C ~H31C02Me
*
*+
94%
C 15H31CH20H
FIPA = 1,1,1,3,3,3-hexafluoropropan-2-ol Teunissen, H.T.; Elsevier. C.J, Chem. Lett., 1998, 1367.
6
NaSMe ,MeOH ,27"C C7H1.5-SAC * C7H15-SH Wallace, O.B.; Springer, D.M. Tetrahedron Lett., 1998, 39,2693.
5% Bi(1II)-mandelate ,DMSO 95"C, 31 h
NO2
NO2
91%
%%
Le Boisselier, V.; Postel, M.; DuAach, E. Tetrahedron Left., 1997, 38, 2981. 10%cyclohexene ,Zn(BH&
PhCOzMe
*
PhCH20H
quant
5h
Narasimhan.; Madhavan, S.; Prasad, K.G. Synth. Commun., 1997, 27, 385.
SECTION 39:
0 4 1111n11
ALCOHOLS AND THIOLS FROM ETHERS, EPOXIDES AND THIOETHERS
PhLi ,BF3aEt2, ether
i-pr
OH Bach.;Eilers, F. Eur. J. Org. Chem, 1998, 2161. Ph
Ph&Ph H o 'i-h
97%
Alcohols from Ethers
Section 39
a
29
1. Li, 5% DTBB ,THF
3. 2.D20 H20
Bachki, A.; Foubelo, F.;
D
&Tetrahedron Lett., 1998, 39, 7759. PhLi (-)-sparteine ,BFyOEt2, ,-78°C ether
*
0 ' 1 % 9,,, 5 % (48%ee)
Alexakis. A,; Vrancken, E.; Mangeney, P. SynLett., 1998, 1165.
Tavlor, S.K,; Dickinson, M.G.; May. S.A.; pickering, D.A.; Sadek, P.C. Synthesis, 1998, 1133.
A0
(Z-Bu)2AlHN< Li' ,rt , 2 h
* L N Et Et Youn, Y.S.; Cho, I.S.; ChunP B.Y. Tetrahedron Lett., 1998, 39, 4337.
3
70%
(94 6) 88% Sreekumar.;Padmakumar, R.; Rugmini, P. Tetrahedron Len.,1998, 39, 5151. ,,,ui\\~
PhLi , 5 % c h i d Schiff base
quant (90%ee)
*
Ommi.
1. Hg(OAc)2, THF-H@ 2. NaBH4, aq K2CO3
b
L
O
O
NJMiyagi, Y.; Itoh, K. Tetrahedron Lett., 1998, 39, 9023.
o
M
e
Crouch.;Mitten, J.V.; Span, A.R.;
Ph H
% %
OH Tetrahedron Len., 1997, 38, 791.
30
Section 39
Compendium of Organic Synthetic Methods, Vol 10
20 min ,139"C
82%
+ ethylene glycol
1h ,228"C 56% Ousaid, A.; Thach, L.N.; LOUDV. 4.Tetrahedron Lett., 1997, 38, 2451.
NaBH4,12, THF ,0°C
Ph-0-
*
3%
Ph-OH
95% Tetrahedron Lett., 1997, 38, 4721.
Thomas, R.M.; Mohan, G.H.; THF,O"C,18h
20%
*Q H
*
QoH 89% (94% ee)
Li
a;. Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett., 1997, 38, 6425. MnMqLi
80%
THF Tang, J.; Yorimitsu, H.; Kakiya, H.; Inoue, R.; Shinokubo, H.; Tetrahedron Lett., 1997, 38, 901 NaBH4,zrCI4,2-proline 3h
60% (44% ee ,RS)
Laxmi, Y.R.S.; Ivengar. D.S. Synth. Commun., 1997, 27, 1731.
Section 39
Alcohols from Ethers
(-)-sparteine , B S i ether, -78°C
31
* H
m . ;Lee, C.P. Tetrahedron Asymmetry, 1997,8, 2307.
81% (70% ee)
78%
Yadav.; Srinivas, D. Chem. Lett., 1997,905. polymer supported AlClZ(BH4)
-OH * Ph EtOH ,reflux Tamami.;Lakouraj, M.M.; Yeganeh, H. J. Chem Res. (S), 1997,330. P h q o
98%
Sarangi, C.; Das. N.B,; Nanda, B.; Nayak, A.; Sharma, R.P. J. Chem. Rex, (S), 1997,378. BaCl c 1 6 H 3 3 q 0
Tc1
THF 81% OH Yasue, K.; Yanagisawa, A.; Yamamota. H, Bull. Chem. SOC.Jpn., 1997,70, 493.
Zn(BH&, AlPO4-1073
ph*OH 97%
Camnelo.; Chakraborty, R.; Marinas, J.M. Synth. Commun., 1996,26, 415. 3 eq (IR,ZS)-norephedrine 6 eq BuLi , PhH/THF 0°C + 25"C, 12 h
Ho
*
&&son. D.M,; Gibbs, A.R. Tetrahedron Asymmetry, 1996,7,407.
OH 63% (99% ee)
32
Section 40
Compendium of Organic Synthetic Methods, Vol 10
2.4 eq i-PrLi ,(-)-sparteine
77% (83% ee)
ether, -98°C + 25°C
c Q0
Hodgson.; Lee, G.-P. Chem. Commun., 1996, 1015.
H
1.5 eq Dibal , 1% NiCl;?(dppp) toluene, 0°C + rt , 2 h
Me0
Taniguchi, T.; -a.
OMe
90%
K, Angew. Chem Int. Ed., 1998, 37, 1136.
bSPh Me3Al, h e m e , 0°C , 3 min
72% Liu, C.; Hashimoto, Y.; Kudo, K.; Saieo. K, Bull. Chem. Soc. Jpn., 1996, 69, 2095. Additional examples of ether cleavages may be found in Section 45A (Protection of Alcohols and Thiols). REVIEWS: "Lewis Acid Induced Rearrangement of l-Hetero-2,3-epoxides. Synthesis, Reactivity and Synthetic Applicationsof Homochid Thiiranium and Aziridinium Ion Intermediates." SynLett., 1997, 11. "Dealkylation of Ethers. A Review." Ranu.; Bhar, S. Org. Prep. Proceed. Int., 1996, 28, 372.
SECTION 40:
CuHzBr
ALCOHOLS AND THIOLS FROM HALIDES AND SULFONATES 2% (C&3CHgHi)$nH,
CO , 90"C, 3 h
AIBN ,NaBH3CN &uJ.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Tetrahedron Lett.. 1997. 38. 7883.
*
cBH270H
42%
33
Alcohols from Ketones
Section 42
02, NaBH3CN, t-BuOH BU
10% t-BuSnC1Bu;l, 33"C,
64%
Sawamura, M.; Kawaguchi, Y.;Sato, K.; m u r a . E. Chem Lett., 1997, 705.
SECTION 41: ALCOHOLS AND THIOLS FROM HYDRIDES
e- ,80%aq MeCN ,LiC104 ,0, 'Il(tfa)3, hematopofphyrin
Maki, S.; Konno, K.;
Tetrahedron Lett., 1997, 38, 7067.
1) 67%
(3
Martin, A.;
- ;Jacquesy, J X . Tetrahedron LRtt.,
1996, 37, 2967.
@
Mn d MeCN e n catalyst, ,rt cat PhIO
Hamachi, K.; Me, R.; Katsulu'.T, Tetrahedron Lett. 1996, 37, 4979.
25% (36%ee ,R)
OH
SECTION 42: ALCOHOLS AND THIOLS FROM KETONES The following reaction types are included in this section: A. Reductions of Ketones to Alcohols B. Alkylations of Ketones, forming Alcohols
Compendiumof Organic Synthetic Methods, Vol 10
34
Section 42A
Molander. G.A. ; Alonso-Alija, C. Tetrahedron, 1997, 53, 8067 Coupling of ketones to give diols is found in Section 323 (Alcohol -+ Alcohol).
SECTION 42A: REDUCTION OF KETONES TO ALCOHOLS ASYMMETRIC REDUCTION
1
Ph
OH
,2.5% i-PrOK
2% 0.25% [RuCl(arene)]z, i-prOH
-A
quant (94% ee , s)
ph
arene = hexamethylbenzene Alonso, D.A.; Guijarro, D.; Pinho, P.; Temme, 0.; J. Org. Chem., 1998, 63, 2749. For an identical reaction using B(OMe)3 and BHySMe2, see Pinho, P.; Guijarro, D.; Anderson. P.G. Tetrahedron, 1998, 54, 7897.
4 A
i-PrOH , KOH
* x
72% (81% ee ,R) Ph a-amino acidate Ru(I1) catalyst Ph Ohta, T.; Nakahara, S.-i.; Shigemura, Y.; Hattori, K.; Furukawa. I. Chem. Lett., Z998,491. H2, [Rh(cod)Cl]2,2,6-lutidine,20°C
-J ,
93% (95%ee) bis-phosphine complex ,MeOH , 1 d ph Ph Jiang, Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang. X, Angew. Chem. Int. Ed., 1998, 37, 1100. PhNEt2BH3 , toluene Ph M e'
% ?h6;
85% (97% ee) Ph M e'
Me Salunkhe, A.M.; Burkhardt. E.R, Tetrahedron Lett., 1997, 38, 1523.
35
Reduction of Ketones
Section 42A
QH -
S-BWAP/(cod)Ru(2-methylallyl)2 H2, autoclave, MeOH , HBr
sph
-
D
M
S
p
h
quant (96% ee) Tranchier, J.-P.; Ratovelomanana-Vidal, V.; CenEt. J.-P.: T o w STetrahedron Lett., Z997, 38, 2951. H2 (lobar), 30min, 1 d 1% (Ru(P*P)C12)2 COzMe
a
C02Me
R,R-SKEWPhoS
P*P = chiral aryl bis-phosphine
Blanc, D.; Henry, J.X.; Ratovelomanana-Vidal, V.; GenCt, J.-P. Tetrahedron Lett., 1997, 38, 6603.
-1
NPN tridentate ligand + RuCldPPh3)~
Ph i-prOH ,KOH Jiang, Y.; Jiang, Q.; Zhu, G.; ZhmgJ.
quant (89% ee)
72% (79% ee)
Ph Tetrahedron Lett., 1997, 38, 215.
Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; N&mLR J. Am. Chem. SOC.,1996, 118, 2521.
ii
H2, chiral Rh catlayst, 82°C
Ph Langer, T.;
4
Ph
*J 4
P Tetrahedron Lett., 1996, 37, 1381.
71% (87% ee,R)
1. 0.5% [Rh(~od)Cl]z,R-DIPOF
ether, PhSiH2
2.H+
P
quant (96%ee ,R )
DIPOF = (SSS)-[2-(4,5-diphenyl-4,5-dhydro1,3-oxazol-2-yl)ferrocenyl]diphenylphosphine Nishibayashi, Y.; Segawa, K.; Takada, H.; Ohe, K.; Uemura. S, Chem. Commun., Z996, 847
36
Compendium of Organic Synthetic Methods, Vol10
a
Ph
, THF
1. 10%
Section 42A
86%(82% ee ,R)
1% IRh(d)c1]2 , 4
2.1M HCl ,MeOH Newman, L.M.; ; McCague, R.; Potter, G.A. Tetrahedron Asymmetry, 1996, 7,1597.
1. 0.4
-r (1 -
~aph~hP
,THF
0.3% [Rh(~od)C1]2,10°C 2. 1M HCl
94% (81% ee ,R) Langer, T.; Janssen, J.; H & ~ ~ E L G Tetrahedron Asymmetry, 1996, 7,1599.
JyJ
Co(I1) complex, NaBH4, EtOH
Me0
/
* 9CHC13
(&OH
-
/
Me0
-2O"C, 1 d
98% (93% ee) Sugi, K.D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett., 1996, 737.
NON-ASYMMETRIC REDUCTION 5% Pt/C , aq KOH TEBA , 1 2 h 95%
Selva, M.; Tundo.;Perosa, A. J. Org. Chem, 1998, 63, 3266. EtOH ,NaI ,e-
*
O
O
Wei-Done. Y.; Cli, Y.; Ar-Xing, W. Synth. Commun., 1998, 28, 2827.
H
75%
Section 42B
Alkylation of Ketones
NGH4, moist Al@3
37
1
6
+ 98% Ph heme Ph Yakate, S.; Hirano, M.; Morimoto, T . Can. J. Chem., 1998, 76, 1916. Y-zeolite-Zn(BH4) 2 0°C , 12 h
82%
. R,; Padmakumar, R.; Rugmini, P. Tetrahedron Lett., 1998, 39, 5151.
A
NaBH4-Alfl3, microwaves, 30 sec
Ph
*
arma. R.S.; Saini, R.K.Tetrahedron Lett., 1997, 38, 4337.
NaBHdAmberlyst-15, THF
1
Ph
87%
* hP' 98% 10 min Ph Ph Caycho, J.R.; Tellado. F.G.: de Marma. P,; Tellado, J.J.M. Tetrahedron Lett., 1997, 38, 277. Ph
a
Ph
PhTMe'BH4, CHzCh, reflux
* PhA
Ph
Firouzabadi.; Adibi, M. Synth. Commun., 1996, 26, 2429.
P
h
91%
SECTION 42B: ALKYLATION OF KETONES, FORMING ALCOHOLS Aldol reactions are listed in Section 330 (Ketone-Alcohol)
EtzZn ,Me$iC1,4 h CHzC12, -20°C Alvisi, C.; Casolari, S.; Costa, A.L.; Ritiani, M.; J. Org. Chem. 1998, 63, 1330.
*$-
. ..
77%
38
Section 42B
Compendium of Organic Synthetic Methods, Vol 10
PhCHO ,cat Tic14 toluene, rt
&
Doas, P.I.;
Fu.
HO
(97 (955 syn:anti? G.C. J. Am. Chem. SOC.,1998, 120, 445.
3) 83%
cyo.".
2eqE~m2;5;$ypTHF *
78%
'444,
I Stiidemann, T.; Ibrahim-Ouali, M.; Cahiez, G.; Knochel, P. SynLett., 2998, 143.
A
Ph
I-""
,THF,rt
bipyridyl ligand , NiC12/CK12 * SynLett., 2998, 1311. 1. PhOH ,45"C
2. acetophenone Yasuda, M.; Kitahara, N.; Fujibayashi, T.;
*
" Ph
Ph
L
B
99%
u
>99% OH
without phenol, yield is 4% Chem. Lett., 2998, 743.
(0 2 eq BuLi/BeClz/THF/O"C 2 eq BuLi/BeC12/ether/O0C (100 Krief. A,; de Vos, M.J.; De Lombart, S.; Bosref, J.; Couty, F. Tetrahedron Lett.. 2997. 38. 6295.
100) 71% 0) 51%
h~~ 6
Section 44
Alcohols from Akenes
2 EtzZn , 5 % MnBrz 3%6o°C, CuCl,30 DMPU min *
39
82%
Riguet, E.; Klement, I.; Reddy, Ch.K.; Tetrahedron Lett., 1996, 37, 5865.
-
1. MeLi-CeC13, THF , -78°C 97%
Bartoli.; Bosco, M.; Van Beek,J.; Sambri, L.; Marcantoni, E. Tetrahedron Lett., 1996, 37, 2293.
a/
2eq
Ph
''-
,20h
[V~c13(thf)612 [ZnCbl
Eataoka. Y,; Makihara, I.; Tani. K, Tetrahedron Lett., 1996, 37, 7083.
97%
MezAo N
,PhH
t
Me2
Ph hP'
P h T M e
80°C, 2 h
Ph 93% Baidossi, W.; Resenfeld, A.; Wassermann, B.C.; Schulte, S.; &humann. H.: Blum. J. Synthesis, 1996, 1127.
SECTION 43: ALCOHOLS AND THIOLS FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION 44: ALCOHOLS AND THIOLS FROM ALKENES
dPh
Ph$b,hv
,Oz
-
P h y Ph CC14,4 h OH Kakusawa, N.;Tsuchiya, T.; &l& Tetrahedron J, Lett., 1998, 39,9743.
48%
40
Section 45A
Compendium of Organic Synthetic Methods, Vol 10
1 . 2 eauiv catecholborane 104 MeCONMe2, RT CH2Clz,3 h ~~H~~C ' H
fic1oH21
95%
2. ox Garrett, C.E.; Fu. G.C,J. Org. Chem, Z996,61, 3224.
"L
Et3A1, W E , 25°C , 4 h
65% (68% ee) J. Am. Chem. SOC., 1996,118, 1577.
2-02 Kondakov, D.Y.; &g&i&
A
Ph
Et
a(BH4)2, SiO2-773 DME
P
i-
P
h
X
O
H
(35 65) 93% Camnelo. J.M,; Chakraborty, R.; Marinas, J.M. Synth. Commun., Z996,26, 1639.
SECTION 45:
ALCOHOLS AND THIOLS FROM MISCELLANEOUS COMPOUNDS NO ADDITIONAL EXAMPLES
SECTION 45A: PROTECTION OF ALCOHOLS AND THIOLS
4
W C l , MeOH (85%) Yadav.;Srinivas, D.; Reddy, G.S. Synth. Commun., 1998,28, 1399. expansive graphite, MeOH
90%
* CsH170H 50°C ,0.7 h Zhang, Z.-H.; Li. T.-S.; Jin, T.-S.; Wang, J.-X. J. Chem. SOC.(SJ, 1998,152. CsHI.pTHP
94%
41
Protection of Alcohols
Section 45A
CBr4, MeOH ,reflux , 2 h Ph-0SiMQt-Bu * Ph-OH Lee. A.S.-Y,; Yeh, H . 4 . ; Shie, J.4. Tetrahedron Lett., 1998, 39, 5249.
90%
1. BusnO 2. PhCOCl
99%
3.H20 Tetrahedron Lett., 1998, 39, 5601.
Maki, T.; Iwasaki, F.; Ph-OH
dihydropyran ,CH2C12, rt
Ph-oTHP
.t
94%
Zr(O3OMe) 1.2(03&H1 iS03H)as curini, M.: Epifano, F.; Marcotullio, M.C.; Rosati, 0.; Costantino, U. Tetrahedron Lett., 1998, 39, 8159. Ph-OH Babu, B.S.; EjdasuF
dihydropyran ,5M LiClOdether rt, 12h
*
Ph-0THlJ
J& Tetrahedron Lett., 1998, 39, 9281.
QH
PTf
1t-Bu
I
86%
83% t-Bu m;Bigot, A.; Dau, M.E.T.H. Tetrahedron Lett., 1997, 38, 1181.
PhMOBn
PhO -H
THF , -25°C
Liu. H.-J,; Yip, J.; Shia. K.-S, Tetrahedron Lett., 1997, 38, 2253.
85%
BnBr , Ag20 CH2C12,15 h Bouzide. A.: SauvB. G. Tetrahedron Lett.. 1997. 38. 5945.
10%
8%
42
Compendium of Organic Synthetic Methods, Vol 10
DMAP , (SiMe3)$iC1
C9H19-OH
\
85% +
Section 45A
c9H19" 0 ~ i ( ~ i ~ e 3 3
hv,MeOH orTBAF
/
68%
Brook.; Gottardo, C.; Balduzzi, S.; Mohamed, M. Tetrahedron Lett., 1997, 38, 6997. BnBr ,CsF , DMF
Ph-OSiMe2r-Bu
+
rt, 12h
Ph-OBn 93%
Orivama. T,; Noda, K.; Yatabe. K. SynLett., 1997, 701. OMe
95%
O /' Ph Bouzide, A.; SauvC, G. SynLett., 1997, 1153.
K10-montmorilloniteclay P
h
4
1
*
PhCHO
96%
acetone, reflux ,30 min
also works with ketals Li, T.-S.; Li. S.-H,Synth. Commun.,Z997, 27, 2299.
OTBDMS (CH2)30TBDMS
LiBr , 18-c-6 85"C, 2 d sealed tube
(CH2hOH
(92 Tandon, M.; Beglev. T.P. Synth. Commun.,1997, 27, 2953.
c@170gMe
10%Yb(OTQ3,MeOH ,RT
(CH2)30TBDMS
8) 75%
+ Ca17-OH 80% Hanamoto, T.; Sugiomoto, Y.; Yokoyama, Y.; InanagaJ..Org. Chem., 1996, 61,4491
Section 45A
Protection of Alcohols
6
H20, DMSO ,LiCl 90°C, 6 h
-
43
j *
D
O
Maiti, G.; Roy, S.C. J. Org. Chem., 2996, 61, 6038. OTBDMS
D::;,"h"-
/
/
OMe OMe Maiti, G.; Roy. S.C, Tetrahedron Lett., Z997, 38, 495.
w
H
83%
81%
DDQ , CH2Clz,lO% H@
* C10H210H 92% rt, 18h YadavXL; Chandrasekhar, S.; Sumithra, G.; Kache, R. Tetrahedron Lett., Z996, 37, 6603. CIoH21
C02Me
OSiMe3
cp
Wilson, N.S.;
5% PdC12(MeCN)2,5 H f l 75"C, 14h
-
0:
Tetrahedron Lett., Z996, 37, 153. PPL ,pH 6.9 buffer, 101h
c02me
c::
OH
82%
Houille, 0.;Schmittberger, T.; uguen, D, Tetrahedron Lett., Z996, 37, 625.
Ti(Oi-pr),
3 BuMgCl
n Lee, J.; €haJL
*HO ' 94%
Tetrahedron Lett., 1996, 37, 3663.
93%
44
Compendium of Organic Synthetic Methods, Vol 10
Section 45A
CAN, MeOH 0°C , 2 . 5 h
Datta Gupta, A.; Singh, R.;
95%
S y n k t t . , 2 9 9 6 , 69.
1. EtsSiOTf , CHzClz
PhMOTHP
0%, 1.-Pr H
b
* PhM O S i E t r
2. NEt3
-a.
77% T.; Yatabe, K.; Sugawara, S.; Machiguchi, Y.; Koga, G. SynLett., 1996, 523.
PhCHzOH
dihydropw , CuC12
*
PhCHZOTHP
*4
CHzCh Bhalerao, U.T.; Davis, K.J.; Rao. B.V, Synth. Commun.,2996, 26, 3081.
&
OTBDMS Vaino, A.R.;
12,
MeOH, 3 h
Chem. Commun., 2996, 2351. CHz(OMe)Z, CHzClZ
Ph-OH
Envirocat EPZG ,40°C, 14 h
OH
* Ph-0-OMe 90%
Bandrrar. B.P.; Hajare, C.T.; Wadgaonkar, P.P. J. Chem. Res. (S), 1996, 90. REVIEW : "Selective Deprotection of Silyl Ethers." Nelson, T.D.; Crouch, R.D. Synthesis, 2996, 1031.
94%
83%
Compendium of’Ovganic Synthetic Methods Micheal B. Smith Copyright 02002 by John Wiley & Sons, Inc
CHAPTER 4 PREPARATION OF ALDEHYDES
SECTION 46:ALDEHYDES FROM ALKYNES
-
-
NO ADDITIONAL EXAMPLES
SECTION 47: ALDEHYDES FROM ACID DERIVATIVES
Ph
CO2H
1 . TMSCl ,N E t 3 , CH2C12,O"C 2. Dibal , -78°C
*
Ph
CHO
83% drasekhar. S.; Kumar, M.S.; Muralidhar, B. TetrahedronLet?,1998,39,909.
PhCH2C02H
ClaycopHfl2 ,microwaves , 1 min
Varma.;Dahiya, R. Tetrahedron Lett, 1998, 39, 1307.
+
PhCHO
83%
HCOOH ,NHqOH ,N2 rt , 3 0 min
90%
Shamsuddin.;Zubairi, Md.0.; Musharraf, M.A. TetrahedronLett., 1998,39,8153. BuGnH, Ni(dppeKl2
PhCHO THF ,25"C M i i h g a L ; Mannucci, S.; Lardicci, L. TetrahedronLett, 1997, 38, 8093.
CSH 1 4 0 2 H
1. heat 2. Na ,EtOH
3. H+ ; H f l
t
Shi. Z,; Gu, H. Synth. Commun., Z997, 27, 2701.
CPlP-CHO
90%
79%
Compendium of Organic Synthetic Methods, Vol10
46
Section 48
SECTION 48: ALDEHYDES FROM ALCOHOLS AND THIOLS P A P , MS 4A.toluene
PhO -H
*
mCHO 70%
Ph
02,70°C TPAP = tetrapropylammoniumpermthenate Mahnvald. R,; Giindogan, B. J. Am. Chem. Soc., 1998, 120,413. also with ketones
PhCH20H
1% [Cn*Ru(CF$Oz)yH201 CH2C12, TBHPDCE ,rt , 12h
Cn* = N,N,N-trimethyl-l,4,7-triazacyclononane
*
PhCHO
88% (70% conversion) also, with 2" alcohols to ketones Fung, W.-H.; Yu,W.-Y.; (&. C.- K J . Org. Chem., 1998, 63, 2873. PhCH20H
DMCC/alumina , cyclohexane
L PhCHO 93% 30°C, 12 h DMCC = dimethylammonium dichlorochromate Zhang.; Shi, Q.-Z.; Chen, M.-F.; Cai, K. Org. Prep. Proceed. Int., 1998, 30, 215.
02,
K2CO3 , PhF , 5 % CuCl
+ C& NCHO 65% Phen , 5 % DBAD ,8O0C Mark6. 1.E; Gautier, A.; Chell6-Regnaut, I.; Giles, P.R.; Tsukazaki, M.; Urch, C.J.; Brown, S.M. J. Org. Chem., 1998, 63, 7576. cfl19cH2oH
* 0 2 , toluene, 75"C, 1h Hinzen, B.; Lenz, R.; Lev. S.V, Synthesis, 1998, 977. (isoquinoline-H)' Cr207-'
* C& BCHO AcOH , CH2C12 Srinivasan, R.; Akila, S.; Caroline, J.; Balasubramanian. K.K, Synth. Commun., 1998, 28, 2245. C7H 1SOH
Ce02RuC13 , 0 2 , toluene PhCHzOH Vocanson, F.; Guo, Y.P.; m v . J.-J..: PhCH20H
*
LHU
64%
PhCHO 80% Synth. Commun., 1998, 28, 2577.
PhI(OAc)2-alumina , microwaves
. t PhCHO 2 min \larma.; Saini, R.K.; Dahiya, R. J. Chem. Res. (S), 1998, 120.
94%
Section 48
wet Cr03-Al203 ,microwaves
ph-OH
47
Aldehydes &om Alcohols
PhCHO
t
76%
Varma. R.S,; Saini, R.K. Tetrahedron Lett., 1998, 39, 1481. Ru(PPh3)3C12, hydroquinone C6H13-OH
C g 1 3-CHO
PhCF3, K z C q , 60°C. 20 h
90% Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii. Y, Tetrahedron Lett., 1998, 39, 5557. 5% Pd(OAc)z, Py
,02
toluene, MS 3A, 80"C, 2 h 95% can also make ketones Nishimura, T.; Onoue, T.; Ohe, K.; Uemura. S, Tetrahedron LRtt., 1998, 39, 6011. NaOCl ,E t O A d H p , 30 min C6H13-OH
ca13
B u m r ,rt
can also make ketones
CHO 86%
Mirafial.;Lozeva, A.M. Tetrahedron Lett., 1998, 39, 7263. P A P , MS 4A, toluene PhO -H also with ketones
02,70°C
*
w
Ph
CHO
TPAP = tetrapropylammonium perruthenate ChellC-Regnaut, I.; Urch, C.J.; Brown, S.M.
woH
~;
J. Am. Chern. SOC., 1997, 119, 12661.
PhI(OAc);!, TEMPO CH~C12~2.5 h
DeMico, A.;. Parlanti, L.; Vescovi, A.; J. Org. Chem., 1997, 62, 6974,
3 t-BuCHO ,MgS04, To1 2% C a @ P h , rt , 4 2 h
Ishihara, K.; Kurihara, H.; Yamamoto. H. J. Org. Chem., 1997, 62, 5664.
85%
70%
Compendium of Organic Synthetic Methods, Vol 10
48
Clayfen, microwaves, 5 sec
PhCHZOH
Section 48
PhCHO
b
92%
also with 2" alcohols
Varma.;Dahiya, R. Tetrahedron Lett., 1997, 38, 2043. MagIrieveTM,CHZC12 L
activated MnOz ,reflux , 4 h
OH
C
PhI(0Ac)z-alumina ,microwaves 1min (no solvent)
O
90%
Magtrieve = magnetically retrievable Cr oxidant Tetrahedron Lett., 1997, 38, 3857.
Lee.; PhCH20H
H
c
PhCHO
94%
Varma.;Dahiya, R.; Saini, R.K. Tetrahedron Lett., 1997, 38, 7029.
MnOySiOz ,microwaves, 20 sec PhCHzOH e PhCHO Varma. RS,; Saini, R.K.; Dahiya, R. Tetrahedron Lett., 1997, 38, 7823. &03,
88%
m+cfi3cl-
c PhCHO 96% U)"C,lh Zhanp. G.-&; Shi, Q.-Z.; Chen, M.-F.; Cai, K. Synth. Commun., 1997, 27, 953.
PhCHZOH
PhCH20H
NH4' CrO3Cl-, SiO2 ,30"C
e
PhCHO
95%
can also form ketones Zhanp.;Shi, Q.-Z.; Chen, M.-F.; Cai, K. Synth. Commun., 1997, 27, 3691. DMF ,KzCrzO7
* MCHO 100°C. 2 h Lou. J.-D,; Lu, L.-H. Synth. Commun., 1997, 27, 3701. O -H
PhCHZOH
10%TPAP , 02 , CH2C12, MS 4A, rt
*
PhCHo
98%
also for ketones Lenz, R.; LGJ-&Y. J. Chem. Soc., Perkin Trans. 1, 1997, 3291. PhCH20H
NbCls, PPA , Hz02
e PhCHO BWOH de Souza Batista, C.M.; de Souza Melo, S.C.; Gelbard, G.; Lachter. E.R. J. Chem. Res. (S), 1997, 92.
86%
Section 48
49
Aldehydes from Alcohols
K2Crz07. PhH , Hz0
PhCHzOH
75T, 8h
Lou. J.-D, J. Chem. Res. (S), 1997,206. NCS ,lo%TEMPO
%HI~\/c\ OH
TBACl , H20, CHg12 pH 8.6,3.5h
-
86%
PhCHO
also for ketones
C6Hl V C H O
quant Einhorn. J,; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem., 1996,61, 7452.
quant
Kaneda.;Fujii, M.; Morioka, K. J. Org. Chem, 1996,61, 4502. O -H
CrO3, Si02, DCE ,n
w
C
10 min
Khadilkar., Chitnavis, A.; Khare, A. Synth. Commun., 1996,26, 205.
H
O
69%
ABTS = 2,2'-azino'bis-(3-ethylbenmthiazoline)-6-sulfonicacid Rosenau, T.; Potthast, A.; CZhen.; Gratzl, J.S. Synrh. Commun., 1996,26, 315.
A \
Ph
Lee.; Lee, J.A.;
NaBH4, BiC13 ,EtOH ,rt ,5h
* PhA Sohn, S.Y.Synth. Commun., 1996,26, 543.
OzgUn, B.; D$innenbqi, N. Synth. Commun., 1996, 26, 3601.
80%
Compendium of Organic Synthetic Methods, Vol 10
50
Section 51
REVIEW: "On the Use of Stable Organic Nitmxyl Radicals for the Oxidation of primary and Secondary Alcohols." deNooy, A.E.J.; Besemer, A.C.; Bekkum. H,Synthesis, 1996,1153.
SECTION 49:ALDEHYDES FROM ALKYNES Conjugate reductions and Michael Alkylations of conjugated aldehydes axe listed in Section 74 (Allcyls from Alkenes). NO ADDITIONALEXAMPLES
Related Methods:
ALDEHYDES FROM ALKYLS, METHYLENES AND ARYLS
SECTION 50:
P
O
A
Aldehydes from Ketones (Section 57) Ketones from Ketones (Section 177) Also via: Allcenyl aldehydes (Section 341)
c
Si02, S Z lmicrowaves I3uOH
P
O
A
c
.
85% Singh. J,; Sharma, M.; Kad, G.L.; Chhabra, B.R. J. Chem.Res. (S), 1997,264.
SECTION 51: ALDEHYDES FROM AMIDES
a
SiazBH ,THF ,25"C
-
PhCHO Ph me2 Godjoian, G.; Sinparam. B, Tetrahedron Lett., 1997,38, 1717.
1. Ti(Oi-Pr)4, PhBiHz, 20°C t
89%
AH
74%
C9H19J m e 2 2. H30+ ,THF qH19 Bower, S.; Kreutzer, K.A.; B u c h w a l d . A n g e w . Chem.Int., Ed., 1996,35, 1515.
Section 54
Aldehydes from Ethers
51
SECTION 52: ALDEHYDES FROM AMINES NO ADDITIONALEXAMPLES Ketones from Amines (Section 172)
Related Methods:
SECTION 53: ALDEHYDES FROM ESTERS NO ADDITIONALEXAMPLES
SECTION 54:
ALDEHYDES FROM ETHERS, EPOXIDES AND THIOETHERS
,RPh A
InC13,THF,rt,lh
Ph
&.
*
H B.C.; Jana, U. J. Org. Chem., 1998, 63, 8212. 10% (CO)zFE(Cp)(thf)+BF4-
Ph
Ph
CHzC12, rt , 3 h
*
M + Ph Ph
CHO
86%
.
OHC99% 92% ee Nozaki.;Itoi, Y.; Shibahara, F.; Shuakawa, E.; Ohta, T.; Takaya, H.; Hiyama, T. J. Am. Chem. SOC.,1998, 120, 4051. e- ,LiC104,80% aq MeCN
Ph Maki.;Niwa, H.; Hirano, T. SynLett, Z997, 1385. Ph*
Wennerberg, J.; Eklund, L.; Polla, M.;
*
PhCHO
71%
Chem. Commun., 1997, 445.
Rh(a~a~)(co)rRSBINAPhos H2/CO (100 a m ) , PhH Horiuchi, T.; Ohta, T.;
'
86% (96% ee) ; Takaya, H. Chem. Commun., 1996, 155.
(PhIO),-HzS04, HzO
h. 0.; Duncan, M.P.; Vaid, R.K.; Rani, N. J. Chem. Res. (S). 1996, 432.
CHO
CHO
44%
Compendium of Organic Synthetic Methods, Vol 10
54
Related Methods:
SECTION 60:
Section 60A
Ketones from Akenes (Section 179)
ALDEHYDES FROM MISCELLANEOUS COMPOUNDS
-
BF3 ,ether PhCHzONO PhCHO & G.. C. S.; Perez, G S.; Zavalas, M.A.; Perez G., R.M.; Guadarrama M, F.O. Synth. Commun., 1998, 28, 3011. BiC13 , HzORHF, 2 min
* PhCHO microwaves Boruah, A.; Baruah, B.; Prajapati, D.; m d h u . J.S, SynLert, 2997, 1251. PhCH=NNMe2
ii+ * PhCH=NaH Baltork. LM,; Pouranshirvani, Sh. Synth. Commun., 1996, 26, 1.
0.1 TsOH*H20 , MeCN ,90"C
85%
. 90%
PhCHO 65%
0 Naka, H.; Sato, S.; Horn, E.; -Heterocycles,
'
*
98%
PhCHO
Tl(NO3)3, MeOH ,rt PhCH=C-NHTs * PhCHO Wane.; Lin, J.; Zheng, Y.; Huang, J. Synth. Commun., 1997, 27, 2583.
97%
1997, 46, 177.
SECTION 60A: PROTECTION OF ALDEHYDES OMe
5% TMSCN(S02Q2
-
PhCHO OMe CH2C12,O"C Kaur, G.; Trehan, A.; Trehan, S, J. Org. Chem., 1998, 63, 2365.
PhCJlO
92%
1% T i c k , MeOH/NEt3 w
0°C ,0.5 h Clerici, A.; Pastori, N.; porta. 0. Tetrahedron, 1998, 54, 15679.
OMe
96%
Section 60A
55
Protection of Aldehydes
FeSO4, toluene, heat, IOmin PhCHO(OAc)2 * PhCHO 98% Jim. T-S.; Ma, Y.-R.;Zhang, Z.-H.; Li. T.-S, Org. Prep. Proceed. Int., 1998, 30, 463.
4x
-
NaBO3, AcOH ,Na2C03
PhCHO
98%
25"C, 1 h W e a r . B.P,; Kulkami, S.A.; Nigal, J.N. Org. Prep. Proceed. Int., 1998, 30, 706. bipy-HCr0$3, MeCN
* PhCHO reflux Kharamesh, B. J. Chem. SOC. (S), 1998, 146.
PhCH2OTHP
93%
vI.: ethylene glycol, I2
PhCHO
microwaves, 7 min also with ketones Kalita, D.J.; Borah, R.; Tetrahedron Lett., 1998, 39, 4573. A c D , zeolite HSZ-360, rt ,70°C PhCHO
* Ph
zeolite HSZ-360, microwaves ,20 min
4
. 99% .
Balhnl.;Bordoni, M.; Bosica, G.; Maggi, R.;
-
>99%
Nishibayashi, Y.; Yamanashi, M.; Takagi, Y.;
w.M. Chem Commun., 1997, 859.
PbgrF5, 60°C, 2 h 91% Chem. Commun., 1997, 1921. PhI(0H)OTs , PdCl2, rt
SnBu:, MeCNM20 A b , H. Tetrahedron Lett., 1996, 37, 3717.
u, "
+
mph S
91%
Compendium of Organic Synthetic Methods, Vol 10
62
.I OH
,Ph
1. BuSnSnBu3, DMF, 80°C Pd(OAc)flPh3 N
I
2. WI , toluene, reflux Pd(PPh3)2C12
*
OHc
N
I
TS
Ts Wang, J.; Scott. A.ILTetrahedron Lett., 1996, 37, 3247. \
Section 67
4 85%
Z&4,2d
a
76%
Me0
Harrowven. D.C.; Dainty, R.F. Tetrahedron Lett. Z996, 37, 3607.
i-Pr
i-Pr
1. BuLi 2. Me1
a
M
e
90%
&?angler.L.A. Tetrahedron Lett. 1996, 37, 3639.
Kita.; Gyoten, M.; Ohtsube, M.; Tohma, H.; Takada, T. Chem. Commun., Z996, 1481. SECTION 66:
ALKYLS, METHYLENES AND ARYLS FROM AMIDES NO ADDITIONAL EXAMPLES
SECTION 67:
ALKYLS, METHYLENES AND ARYLS FROM AMINES NO ADDITIONAL EXAMPLES
Section 68
SECTION 68:
ALKYLS, METHYLENES AND ARYLS FROM ESTERS
c " ' ' 3 ~ 0 A c Q0
63
Alkyls from Esters
It-Bu
2 Et2Zn , 1.5 TMSOTf CHzC12, -78°C , 2 h
inTHF
quant (1:O anti:syn)
t-Bu
91% (5 1:1 antisyn) Pvchnovskv. S.D,; Powell, N.A.. Org. Chem., 1997, 62, 6460. BuguLi , 3 eq BFyOEt2, -78°C I)
+ bp BnO
Me
ether-hexane , 3 eq 0 2
Bu
BnO
Matsutani, H.; Ichikawa, S.; Yarava, J.; Kusumoto.; Hiyama, T. J. Am. Chem. SOC., 1997, 119, 4541.
53% (86%ee - inversion)
10% Ph-oAc Mo(CO)~, A r , 7 2 h 139°C
80% . . Shlmlzu.;Sakarnoto, T.; Kawaragi, S.; Maruyama, Y.; Yamamoto, A. Chem. Lett., 1997, 137.
5% Pd(dba)Z, DMF C6H1
LiCl , Me3SiSiMe3
sihae3
*
C
6
H
l
d
81%(95:5 E:Z)
Funato, M.; Ozawa, M.; Ogiyama, H.; Kajita, S.; Kawamura, T. J. Org. Chem., 1996, 6I,5779.
-;
64
Compendium of Organic Synthetic Methods, Vol 10
Section 69
PhSnBu3 , 2 % Pdz(dba)ydba aq. DMF, l h Ph Ph Castaao, A.M.; Bhavarren. A.M, Tetrahedron Lett., 1996, 37, 6587.
SECTION 69:
ALKYLS, METHYLENES AND ARYLS FROM ETHERS, EPOXIDES AND THIOETHERS
The conversion ROR -+ RR’( R = alkyl, aryl) is included in this section. BuMgBr ,Ni(dppe)Cl,
-
THF , heat
O
B
u
95% Guagnmo, V.; Lardicci, L.; Malanga, C.; fvienicaeli. & Tetrahedron Lett., 1998,39,2025.
TBDMS Me0
SiMe3
-
Tic4 85%(>99:1 anfi:syn) Th4SOTf 89% (96:4 unti:syn) Maeda, K.; Shinokubo, H.; Dshima. K, J. Org. Chem., 1997, 62, 6425. Me&-
, e-
Yoshida.; Sugawara, M.; Kise, N. Tetrahedron Lett., 1996, 37, 3157.
61%
Section 70
Alkyls from Halides
SECTION 70:
65
ALKYLS, METHYLENES AND ARYLS FROM HALIDES AND SULFONATES
The replacement of halogen by alkyl or aryl groups is included in this section. For the conversion of Rx + RH Q = halogen) see Section 160 (Hydrides frorn Halides and Sulfonates).
6
=
6 pk Ph
Ph
Ph
5% Pd(OAc)z, 2 eq NaOAc 3 eq Bu&CI ,DMF ,100"C
Larock.;Tian, Q. J. Org. Chem., 1998, 63, 2002. Ph
B-allyl-9-BBNNoKOMe
\
~
86%
3% PdC12(dppf) ,THF reflux
OTf Fiirsmer. A,; Seidel, G. SynLett, 1998, 161.
Ma, J.; Chan, T.-H. Tetrahedron Lett., 1998, 39, 2499. Ph-I
silica supported phosphine palladium (0)
*
81%
Ph-Ph
95%
PhMgBr ,THF ,30"C, 20 h Cai, M.-Z.; Song, C.-S.; J. Chem Rex (S), 1998, 264.
2.1 eq PhZnCl , S O T , 1 d
2% C12Ni(PW&, 4% PPh3 Miller. J.AJ Farrell, R.P. Tetrahedron Lett., 1998, 39, 6441.
75%
a
66
Compendium of Organic Synthetic Methods, Vol 10
4
I
Baruah, M.;
Section 70
95 %
a 6
Boruah, A.; Prajapati, D.; Sandhu. J.S, SynLett, 1998, 1083.
,OM"
Pd(OAc)z/Bu&€3r,K2CO3
OMe
aq DMF, i-PrOH , 8 h
*
*&)
81%
/
Me0 Penalva, V.; Hassan, J.; Lavenot, L.; Gozzi, C.; LeMaire. M, Tetrahedron Lett., Z998, 39, 2559
6
M S~(0Tf)3,80"C ea
Me
Kotsukl.;Oshisi, T.; Inoue, M. SynLett, 1998, 255.
lcJ(
MgC1
CN
, 6 %ZnC12
6%[Ni(acac)$(i- PrO)3P/ether/MeMgCI]
Miller. J.A.; Farrell, R.P. Tetrahedron Lett, 1998, 39, 1215,
*d 82%
Section 70
67
Alkyls from Halides
I
3eq Me
6'
1% Pd(dba)z, NaOH ,75"C aq acetone
Tsarev, D.A. Tetrahedron Lett., 1998, 39, 8155.
;-
In, DMF, reflux, 8 h
Ph-1
*
Ph
Ranu.; Dutta, P.; Sarkar, A. Tetrahedron Lett., 1998, 39, 9557. hv , AIBN , PhH
I
ph
89%
a v e . D . U ; Paul, C.C.; Wang, Z. J. Org. Chem., 1997, 62, 7028.
(I
3% Pdz(dba)j , 4 PPh3 To1 , 101"C, 12 h
t-Bu
76%
i-Bu
m; Pereyre, M.; Rodriguez, A.L. J. Org. Chem., 1997, 62, 5242.
ASAb
Ph
02
1. LiOt-Bu , THF
*
2. aq NH4Cl
Berkowitza.;Wu, Y. Tetrahedron Lett., 1997, 38, 3171.
PhA
O 75% (9:l E:Z)
H
Compendium of Organic Synthetic Methods, Vol 10
68
($
Section 70
PhMnCl , PdC12(PPh3)2,
/
/
DME
91% OMe Tetrahedron Lett., 1997, 38, 4397.
OMe Riguet, E.;
PhB(OH)2, lOo"C, 10 h Pd(OAC)z, dppp NO2 m n . W. Tetrahedron Lett., 1997, 38, 5575.
92%
NO2
PhMgBr ,PdCl2(alaphos), 3 h
* OTf Kamikawa, T.;
.
a
P
h
95%
Ph
SynLett, 1997, 163.
NaCMe(CO2Me)2, THF 2%PdCl(xC3H5)2, dppe Ph
OAc
-20°C
Ph (7 9
Ph
with R-MeOMOP Favashi. T,; Kawatsura, M.; Uozumi, Y. Chem. Commun., 2997, 561.
PhZnBr ,0.6%P(Ar)3,6OoC 0.15% Pd(dbah ,toluendcgH17Br OAc Ar = p-C&ghenyl OAc Betzemeier, B.; K n o c h e l . A n g e w . Chem. Int. Ed., 2997, 36, 2623.
93 %
93) 92% 1) 96%
Section 70
69
Alkyls from Halides
I
DMI ,NaOC85, CuI , 130°C does not work well with all SiR3derivatives
Ito, H.; Sensui, H.; Arimoto, K.; Miura, K.; JIosomi, A. Chem. Lett., 1997, 679.
.
Hara, R.; Sun, W.-H.; Nishihara, Y.;
72%
Chem. Lett., 1997, 1251.
F$i--c6H13, 5% Pd(PPh3)4
4eqTBAF,THF,100°C
65%
Matsuhashi, H.; Asai, S.; Hirabayashi, K.; Hatanaka, Y.; Mori, A.; Bull. Chem. SOC. Jpn., 1997, 70, 437. Me0
74%
ClCH2C@Me , e- ,DMF Ni cathode, NBu4BF4, NiBqbipy Nkdekec, J.-Y.; Perichon, J. J. Org. Chem, 1996, 61, 1748.
;-
I
II
dM
D
6 KF ,0.5% (i-Pr3PhPdClz DMF , 120"C,2 d
M
Me0
62%
Gouda, K.; Hagiwara, E.; Hatanaka.;Hiyama, T.J. Org. Chem., Z996, 61, 7232.
Compendium of Organic Synthetic Methods, Vol 10
70
6
2.1 eq CuCl , 3 eq DMPU iO"C, THF , 1 h
-1
Section 70
i
Et
m; Ham, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc.. 1996, 118, 5154. 10% K NiClZ(dppf), 3 F Q Z4 eq 80°C BuLi
B(oH)2
CN 74%
Saito, S.; Sakai, M.;
Br
Tetrahedron Lett, 1996, 37, 2993; 1. BuflnMgBr
c 6 H i ~ M e
h
2. Me1
c6H1f%,r
Bu
+
(94 Inmu, R.; Shinokubo, H.; Oshima K., Tetrahedron Lett, 1996, 37, 5377.
4-
1. MeMgCl ,LiCLO4
ether-PhH
Ph
sO2Ph
Giovannini, R.;
6) 65%
2. NH4Cl
*
Ph+CN
75%
SynLett, 1996, 1001.
80% Nishivama. T,; Seshita, T.; Shodai, H.; Aoki, K.; Kameyama, . H.:. Komura K. Chem. Lett., 1996, 549.
PbMgBr , 1%Fe(dbm)3
-
p h w Gai, Y.; Julla.;Vefpeaux, J.-N. Bull. SOC.Chim. Fr., 1996, 133, 805. plI0;s-
88%
71
Alkyls from Ketones
Section 72
/Br OMe
Wang, X.-Z.;
3% p d ( P P l ~ ~100°C )~ 3.3 K3POj.3 H20
a M.-7.
SECTION 71:
OMe
J. Chem SOC., Perkin Trans. 1, 1996, 2663.
89%
ALKYLS, METHYLENES AND ARYLS FROM HYDRIDES
This section lists examples of the reaction of RH -+ RR'(R,R = alkyl or aryl). For the reaction C=CH -+C=C-R (R = alkyl or aryl), see Section 209 (Alkenes from Alkenes). For alkylations of ketones and esters, see Section 177 (Ketones from Ketones) and Section 113 (Esters from Esten). NO ADDITIONAL EXAMPLES
SECTION 72:
ALKYLS, METHYLENES AND ARYLS FROM KETONES
The conversions R2C=O + R-R, R2CH2, R2CHR, etc. are listed in this section.
i i
10%TlC13(OTf),sealed tube 90-100"C, 10 h
99%
Ph
IranDoor. N,; Zeynizaded, B. SynLetr, 1998, 1079.
Ph
Ph
OH
R -
3. aq HCl I
.
Synth. Commun., 1998, 28, 1525.
55%
72
Section 74A
Compendium of Organic Synthetic Methods, Vol 10
L
Pb
1. MeMgBr , VC12(tmeda)-2 z-
2 . 0 2 , THF ,reflux
P
h
k
+’%
89%
11%
Kataoka.; Akiyama, H.; Makihira, I.; W K . Org. Chem., . Z997,62, 8109.
L
Ph
-++x
1. MeMgBr , VCl2(tmeda)2 2 . 0 2 , THF ,reflux 15h
Ph 89% Kataoka.; Akiyama, H.; Makihira, I.; Tani, K. J. Org. Chem., 2996, 61, 6094.
SECTION 73
11%
ALKYLS, METHYLENES AND ARYLS FROM NITRILES 1.3 eq Lilnaphthalene ,THF
2. ally1 bromide 82% Chang, N.-Y.;Yie, J.; Liu, H . 4 . Terrahedron Lett, 1997, 38, 7713.
SECTION 74:
ALKYLS, METHYLENES AND ARYLS FROM ALKENES
The following reaction types are included in this section: A.
B. C. D. E. F.
Hydrogenation of Alkenes (and Aryls) Formation of Aryls Alkylations and Arylations of Alkenes Conjugate Reduction of Conjugated Aldehydes, Ketones, Acids, Esters and Nitriles Conjugate Alkylations Cyclopropanations,including halocyclopropanations
SECTION 74A: Hydrogenation of Alkenes (and Aryls) Reduction of aryls to dienes are listed in Section 377 (Alkene-Alkene).
Section 74A
Hydrogenation
73
(200 , : 1) quant (99.2% t ~ S) Burk.; Allen, J.G.; Kiesman, W.F. J. Am. Chem. Soc.. 1998, 120,657. NHAc
I
NHAc I
S,S-MeBPE-Rh ,H2,O"C
92% ee
Burk.;Casy, G.; Johnson, N.B. J. Org. Chem., 1998, 63, 6084. H2, 1% [Rh(cod)i)BF4, toluene 1.1% A,R-BICP, rt
Ph
*
Phl N H A c 86% ee
Zhu, G.; Zhane. X. J. Org. Chem., 1998, 63, 9590.
chiral diphosphine catalyst 30 psi H2 ,THF
* Ph4
O
A
94% ee
Boaz, N.W. Tetrahedron Lett., 1998, 39, 5505.
n
A
"Q%*,,
H
C
NaBH4,BiC13,EtOH,rt,5h Ph * Ph 80% Ren, P.-D.; Pan, S.-F.; Dong, T.-W.; Wu. S .-& Synth. Commun., 1996, 26, 763. 0.2% -(Me-DPE)(cod)+ Ph
NHAc
60 psi H2
O T f ,MeOH
*
PhN ' HAc
Me-DPE = 1,2-bis(trans-2,5-dirnethylphopholanoethane 95%ee,R Burk. M.J.; Wang, Y.M.; Lee, J.R.J. Am. Chem SOC., 1996, 118,5142.
Compendium of Organic Synthetic Methods, Vol10
74
Section 74C
NiC12.2 H 2 0 , Li" , naphtbalene-THF
*
c s N 1 1
99%
Alonso, F.; Yus. M,Tetrahedron Lett.,1996, 37, 6925. BER-Ni2B ,MeOH , 0°C , 1 h z
quant
Synthesis, 1996, 597.
Choi, J.;
REVIEW: "Asymmetric Transfer Hydrogenation Catalyzed by Chiral Ruthenium Complexes." Novori. R,; Hasiguichi, S. Accts. Chem. Res., 1997, 30, 97.
SECTION 74B: Formation of Aryls
10 eq PhMgBr
-0
Blank, D.H.; Gribble. G.W, Tetrahedron Lett., 1997, 38, 4761.
0
-
Ph
1.25 NCS 2 . 5 NaOMe ,MeOH
94x95%
Ph
DeKimDe, N,; Keppens, M.; Fonck, G. Chem Commun., 1996, 635.
SECTION 74C: Alkylations and Arylations of Alkenes 1 a m CHz=CHz, CHzClz, -56°C
Ph
-1
>95% 0.35% (allylNiBr)2/PPh3/AgOTf, 2h Ph Nomura, N.; Jin, J.; Park, H.; Raianbabu. J.V, J. Am. Chem. SOC., 1998, 120, 459.
aoTf 1.5eqCeH1WgBr7THF 10%Cul,-20"C
*
(
y
1
7
59%
Karlstrom, A.S.E.; Ronn, M.; Thorarensen, A.; Biickvall, I.-E. J. Org. Chem., 1998, 63, 2517
Alkylation of Alkenes
Section 74C
75
Vicart, N.; Castet-Caillabet, D.; Ramondency, Y.;PlB, G.; Cuhame1. L, SynLett, 1998, 411
Jb
&:
2 eq PhSnBu3 , 4 eq ClCH2CqMe cat PdC12(PhCN)2, cat PPh3 THF ,50°C, 29 h
*
*s 58%
Fugami, K.; Hagiwara, S.; Oda, H.; JCOSU~ i. M, SynLett, 1998, 477.
-?
[ (CpTMShYMe 1 2 , THF
rt, 12h
p -
SiHph
4 '8 ,
-92%
Molander.; Dowdy, E.D.; Schmumann, H. J. Org. Chem., 1998, 63, 3386.
Mn* ,THF ,25"C
72% (1:l syn:anfi)
Bu 0 Bu 0 Tang, J.; Shinokubo, H.; QsUnaJL SynLett, 1998, 1075.
OTf
t-Bu
1. PhSnI[N(TMS)2]2,DMF ,5O"C 3 eq B u m
2. 1% Pd~(dba)~ , 4 % AsPh3
m; Rodriguez, A.L. SynLett, 1998, 1323.
L
-7 Br
C&IlWgCl, 3% Fe(acac)3,15 min * THF-DMF , -5°C + 0°C
Cahiez. G,; Avedissian, H. Synthesis, 1998, 1199.
t-Bu 83%
\
81%
c@17
76
Compendium of Organic Synthetic Methods, Vol 10
1'' :1;
Section 74C
*
THF 1 3 ,13 % ~MnC12-2 3 L , LiCl
C5H1 1
(98:2 E:Z)
C5H11
Alami. M.; Ramiandrasoa, P.; u i e z . G,SynLett, 1998, 325.
&Br
BuMgCl , 3% Co(acac)2
Ph
-
mBu
Ph 88% 4 THF-NMP , -5°C + 0°C Cahiez. G; Avedissian, H. Tetrahedron Lett., 1998, 39, 6159. Avedissian, H.; Berillon, L.; Cahiez. G.: Knochel. P. Tetrahedron Lett., 1998, 39, 6163 (with R-Zn derivatives).
Molander. G.A.; Corrette, C.P. Tetrahedron LRtt, 1998, 39, 5011.
4
Ph
EtOTs ,cat Cp2zTc12
*
82%
phy
62%
B uMgCl Et Terao, J.; Watanabe, T.; Saito, K.; Kambe. N.;Sonoda, N. Tetrahedron Lett, Z998, 39, 9201.
alr 0
Bu3MnLi
Nakao, J.; Inoue, R.; Shinokubo, H.; ,C02Me
40%
J. Org. Chem, 1997, 62, 1910.
PhBr ,NEt3, hexaneether, 2 h 3% PdC12-gla~sbeads
/co2Me
54%
_Ph_
Tonks, L.; Anson, M.S.; Hellgardt, K.; Mirza, A.R.; Thompson, D.F.; Williams. J.M.J, Tetrahedron Lett.. 1997. 38. 4319.
Section 74C
77
Alkylation of Alkenes
PhI , CuBr ,K2CO3, NMP 150°C, 1d
_/co2Me
*
C02Me
Ph
a? 75%
u; Ramesh, C.; Sarkar, A.; Wadgaonkar, P.P. Tetrahedron Lett., 1997,38, 8113. PhBr ,Pd(OAc)z, P(o-ToO3
A
Ph
NEtq, microwaves
Ic
&Ph
Ph
quant
Pfaz-Ortiz. A.; Prieto, P.; Vhzquez, E. SynLett, 1997,269.
dC1 ')=
,hv,AgOTf
PhSH ,PhH
60%
Chem. Lett., 1997,843.
Sawayanagi, Y.; Sato, T.;
>""
NaCH(COzMe)z, 120°C 2% (dcypb)PdMe2
3% dcypb dcypb = 1,4-bis(dicyclohexylphosphino)butane
u CO2Me
*
MeOg
Reetz. M.T,; Wanninger, K.; Hermes, M. Chem. Commun., 1997,535.
76%
Phi , Pd on porous glass 18O"C, microwaves
Li, J.; Mau, A.W.-H.;
Ph
(83 : 1 Chem. Commun., 1997, 1275.
CH2=CHCO2Me, PdCu Montmorillonite clay
16) quant
-cF
C02Me
83%
Ramchandani, R.K.;Uphade, B.S.; Vinod, M.P.; Wakharkar, R.D.; Choudhary, V.R.; Sudalai. A, Chem. Commun.. 1997. 2071.
78
fi
&
Section 74C
Compendium of Organic Synthetic Methods, Vol 10
s02Ph
1.5% Pd(PPh3)d
2. Et2Zn
3. aq NH4CI
3
0
2
P
* +#, # '
AcO
I
3. styrene 4. HzO
me2
%#
16) 79%
(84 Oppolzer, W.; Schriider, F.; Kahl, S. Helv. Chin Acta, 1997, 80, 2047.
A\
h
me2 Kubota, K.; Nakamura. E, Angew. Chem. Int. Ed., 1997, 36, 2491. 1. PhCl ,CoBq ,NaI ,DMF ,PPh3 130°C, 4 h
/L'02H
2. Pdddba)3 , PPh3, NEt3 130°C, 20 h 3. H20 Mitra, J.; Mitra. A.K, J. Indian Chem. SOC., 1997, 74, 146.
Ph
52%
PhZI+ BF4- ,DMF , 2 NaHCO3
O -H
*
2% Pd(0Ac)z
PhO -H 87%
Kanp.; Lee, H.-W.; Jang, S.B.; Kim,T.-H.; Pyun, S.-J. J. Org. Chem., 1996, 61, 2604 INi(MeCN)61[BF412,AEt2C1, PPb3 + CH2=CH2, CH2C12,lO bar rt ,30 min
A/
Ph
97%
Monteiro.;Seferin, M.; Dupont, J.; de Souza, R.F. Tetrahedron Lett., 1996, 37, 1157.
AI
Bu
CgH+inCl, 3% Fe(acac)s " M P , 1h
+
cahiez, G,; Marquais, S. Tetrahedron Lett., 1996, 37, 1773
Ac a
Bu
17
90%
c; /
I Larhed. M
CHz=CHC%Me, DMF Pd(OAc)z, 3.8 min microwaves
-
MeOg
FoM 70%
J. Org. Chem, 1996, 61, 9582.
Et3Ga, hexane, rt , 3 h
7
Ph Han, Y.; &mg.
79
Alkylation of Alkenes
Section 74C
68%
#Et
Ph Y.-Z.; Zhou, C.-M. Tetrahedron Lett., 1996, 37, 3347.
1. Et2AlC1, cat Ti(i-Pr)4 , 5OoC 2.02
4
\OH
#""
c&13
c&13
Tetrahedron Lett., 1996, 37, 3803.
Kondakov, D.Y.; Wang, S.;
Knolkner. H.-J,; Jones, P.G.; Graf, R. SynLelt, 2996, 1155.
86%
7 OAc
NHCbz
B u w r , K2CO3, DMF 10%Pd(OAch, 55°C Crisp. G.T.; Gebauer, M.G. Tetrahedron, 1996, 52, 12465.
80%
NHCbZ
64%
q
80
CL
RhCl(PPh&
10 eq BuCH=CHz
llO°C, 19 h
Lim, Y . 4 . ; Kang, J.-B.; SnBu3
0
Section 74D
Compendium of Organic Synthetic Methods, Vol 10
*qJu
99% (93:7 trms:cis) Chem. Commun, 1996, 585.
2 eq Phi , toluene ,reflux 2% C12(PPh3)4pd
0
do 45%
Holingworth, G.J.; Perkins, G.; Sweenev. J, J. Chem. SOC.,Perkin Trans. I , Z996, 1913.
SECTION 74D:
Dh. B,;
Conjugate Reduction of a$-Unsaturated Carbonyl Compounds and Nitriles
g
Kashinatham, A.; Madhusudhan, P. Tetrahedron Lett., Z998, 39, 677.
[(Ph3P)CuH]6,PhSiH3, rt toluene - H2O , 6 h
*
99%
Keith, J.; Papa, P.; Vivian, R. Tetrahedron Lett, 1998, 39, 4627. PhSiH3, PPh3 [NiI&i/THFJ 95% ~.
Boudiouk. P,; Choi, S.-B.; Hauck, B.J.; Rajkumar, A.B. Tetrahedron Lett., 1998, 39, 3951.
Section 74D
Conjugate Reduction
81
SmI2, t-BuOH ,DMA THF ,rt , 3 min does not work with 6-membered ring lactones Fujita, Y.; Fukuzumi, S.; Tetrahedron Lett., 1997, 38, 2121.
1. PhMe2SiH , CuCl ,DMI , rt 2.W)
gPh gPh m C 0 2 E t Ph
/.\\/COZEt
* Ph
DMI = 1,3dimethylimidazolidinone 96% . Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K.; Tetrahedron Lett., 1997, 38, 8887
& H m : :
~
92% (14: 1 syn:anti)
Yamaeuchi. M; Nit@ A.; Reddy, R.S.; Hirama, M. SynLett, 1997, 117. HSiPhMez
> 99% CuF(PPh3)3.2 EtOH Mori. A,; Fujita, A.; Nishihara, Y.; Higama, T. Chem. Commun., 1997, 2159.
L
Ph
ATPH ,DIBAL-H-BuLi ,-78°C 15 min , tol-THF-hexane
ATPH =
..(.
-lit Ph
13
saito, s.; Yamamoto. H,J. Org. Chem., 1996, 61, 2928. HZtoluene , 5 % Cu/Si02,90°C , 2h
99%
Do quant
Ravaslo.; Antenori, M.; Gargano, M.; Mastrorilli, P. Tetrahedron Lett., 1996, 37, 3529.
Compendium of Organic Synthetic Methods, Vol 10
82
6
F,C0$30
DCE
Tetrahedron Lett., 1996, 37,4199.
Nenajdenko, V.G.; Baraznenok, I.L.;
;-
Section 74D
gcN d/: ..
85%
Boscia, G. Tetrahedron Lett., 1996, 37, 8027.
0
NaTeHr ,t AcOH , 2 4 h ,EtOH *
NC Blay, G.; Cardona, L.; Garcia, B.; Lahoz, L.;
NC
Tetrahedron, 1996, 52, 8 1
NaBH4, EtOWdiglyme C02Et
2%cd312,~emicomhligand
90% (93%ee ,R)
Helv. Chim. Acta, 1996, 79, 961.
Misun, M.; NO2
C02Et
yeast , lightpetroleum
Ph Bak, R.R.; McAnda, A.F.;
*
Ph-NO2
74%
; Trewhella, M A . Aust. J. Chem., 1996, 49, 1257
Section 74E
Conjugate Alkylations
83
SECTION 74E: Conjugate Alkylations
2. cat MezCu(CN)Li,
3. PhMezSiCl
SN2Ph
90% Lipshutz. B.H,; Sclafani, J.A.; Takanarni, T. J. Am. Chem. SOC.,1998, 120, 4021.
66% 78) (22 18) 99% with C12BnSn-N(i-Pr)2 (82 Shibata, I.; Yasuda, K.; Tanaka, Y.; Yasuda,M.; Baba. A. J. Org. Chem., 1998, 63, 1334. -NO2 Ph
Et2Zn, toluene, 2% Cu(OTf), 4%BINOL-phosphoramidite
*
Sewald.;Wendisch, V. Tetrahedron Asymmetry, 1998, 9, 1341.
1 Ph
N
90%(48%ee)
EtMgBr , 5 % S,S-chiraphos
5% (PPh3)2NiC12
*
&Et 90% (85%ee) Gomez-Bengoa, E.; Heron, N.M.; Didiuk, M.T.; Luchaco, C.A.; Hovevda. A.H,
J. Am. Chem. SOC..1998. 120. 7649.
0
2
Section 74E
Compendium of Organic Synthetic Methods, Vol 10
84
-A
CeC13.7 H@ ,microwaves
*%
92% 0 Boruah, A.; Baruah, M.; Prajapati, D.; Sandhu. Ls,Synth. Cornrnun., 1998, 28, 653.
MeCHSHCOZH
1.2.2 eq BuLi ,THF , -78°C
2. TFA
Plunian, B.; Vaultier, M.;
*
L
C
a
H
80%
Chern. Commun., 1998, 81.
61.
Kuhnert, N.; Peverley, J.; Robertson. J. Tetrahedron Lett., 1998, 39, 3215. +Oms
Ph
,20% InC13 rt,30min
Lab. T.-P.; Wei, L.-L. Tetrahedron, 1998, 54, 7615. A
*
67%
(-)-sparteine
XULE;; Tillyer, R.D.; Tschaen, D.M.; Grabowski, E.J.J.; Reider, P.J. Tetrahedron Asymmetry, 1998, 9, 1651. &C02H
Ph
BuLi (add acid to BuLi)
Aurell, M.J.; Mestres.; Muiioz, E. Tetrahedron Lett., 1998. 39, 6351.
78% (25% ee)
85
Conjugate Alkylations
Section 74E
CH2C12,12 h
0 80%
Christoffers. J, Tetrahedron Lett., 1998, 39, 7083.
92% (96% ee ,S) Takaya, Y.; Ogasawara, M.;Havashi. T, Tetrahedron Lett, 1998, 39, 8479. . I
1. Sm/NiIz, THF , -78°C 2. t-BuOH
COzEt
97% (>100:1 truns:cis)
Molander.,Harris, C.R. J. Org. Chem.. 1997, 62, 7418.
c1
MAD = (4-Me-2,6-dit-Bu-C&2+)2AlMe
c1
Tucker.;Clayton, T.C.; Morda, D.M. J. Org. Chem., 1997, 62, 4370.
Section 74E
Compendium of Organic Synthetic Methods, Vol 10
86
%
~
Y-zeolite ,rt ,20 min
82%
0
Sreekumar. R.; Rugmini, P.; Padmakumar, R. Tetrahedron Left, 1997, 38, 6557. MezCHNa, NaOt-Bu toluene Ph
Ph
a
Bak6, P.; Kiss, T.;
Ph
Ph
chiral aza-crown catalyst
0 2 ~
73% 961% e e , S) Tetrahedron Lett., 1997, 38, 7259.
phnfph
[PhMe2SiLi/Me2Znl THF , -30°C
PhMe2Si
0
91% MacLean, B.L.; Henningar, K.A.; Kells, K.W.; Singer. R.D. Tetrahedron Lett., Z997, 38,7313
CH2=CHMgBr, TMEDA TMSCl , -78°C + -30°C 83% (>90% de) Han, Y.; m b v . V.J. Tetrahedron Lett., 1997, 38, 7317.
0
0
Kotsuki. H.; Arimura, K. Tetrahedron Lett, 1997, 38, 7583.
95%
Section 74E
Conjugate Alkylations
P h T C N CN
BTCH2CO$t, THF , R ZdCp2TiC12
t
87
Eog+ Ph
83 %
ping. Y,; Zhao, Z.; Zhou, C. Tetrahedron, 1997, 53, 2899.
CN
77% (65% ee ,S)
Alexakis.;Vastra, J.; Burton, J.; Mangeney, P. Tetrahedron Asymmetry, 1997, 8, 3193.
Alexakis. A.; Burton, J.; Vastra, J.; Mangeney, P. Tetrahedron Asymmetry, 1997, 8, 3987.
,no solvent
C02Et
1 % Fedl3-6 H 2 0
*&
J. Chem. SOC.,Perkin Trans. I , Z997, 3141. Chem. Commun., 1997, 943.
1. BuMgCl , THF 0.1 Cu taddol complex 2. H3O+
-4
C02Et
97%
0
50%(70:30 R:S)
Bu eebach. D,; Jaeschke, G.; Pichota, A.; Audergon, L. Helv. Chim. Acta, 1997, 80, 2515.
88
Compendium of Organic Synthetic Methods, Vol10
Section 74E
Bu(TMSM)Zn ,TMSCl ,THF NMP , -20°C -+ 25°C
83%
bn
Bu TMSM = Me3SiCH2 Berger, S.; Langer, F.; Lutz, C.; Knochel.; Mobley, T.A.; Reddy, C.K. Angew. Chem. Int. Ed., 1997, 36, 1496. CH2(COzi-Pr)z, CHC13 , RT 0
Q C 0 2 R b
21h
H
i-p~og
CO2i-Pr
71% (76% ee ,(S) Yamapuchi.; Shiraishi, T.; H u m , M. J. Org. Chem., 1996, 61,3520.
n Ph
TeBu3
oo
1. MezCu(CN)Liz ,THF 2.
L
P
h
90% Tucci, F.C.; Chieffi, A.; Comasseto. J.V. : Marina J.P, J. Org. Chem., 1996, 61, 4975.
88% (88% ee ,R ) Sibi. M.P,; Ji, J.; Wu, J.H.; Giirtler, S.; Porter. N.A,J. Am, Chem. Soc., 1996, 118, 9200.
==TMe
Ca171, MeOH ,rt , 9 h 0.05 NizB-BER
BER = borohydride exchange resin Sim, T.B.; Choi, J.; Yoon. N.M, Tetrahedron Lett., 1996, 37, 3137.
C02Me 88%
Section 74E
Conjugate Alkylations
89
Et
0
C02Et
Yb(OTO3, ether, 5 d
0 Keller, E.;
Tetrahedron Lett., 1996, 37, 1879.
>98%
0
cat CuCN ,THF ,45"C, 8 h
86%
(CsHllhZn, NMP , -30°C
6,
83%
c5H 11
Reddy, Ch.K.; Devasagayara, A.; Knochel. P, Tetrahedron Lett., 1996,37,4495. 1. Me2Zn , BnNHS02Ph CuCN,6h
Kitamurn, M.; Miki, T.; Nakano, K.; = - hP
-tL
90%
2.H20
Me Tetrahedron Lett., 1996, 37, 5141.
acrolein, Pd(OAc)z, LiCl , AcOH
"
V
C
H
O
Ph Wang, 2.; L!L&
77% (955 EE) Chem. Commun., Z996, 535.
90
Compendium of Organic Synthetic Methods, Vol 10
Section 74F
NaCNBH3 , zeolite H-ZSMS pH 6.5 Gupta, A.; Haque, A.; Vankar. Y.D, Chem. Commun., 1996, 1653.
PhMgQ, THF
+
) .
AlMe2C1, -60°C
(90 10) 89% Bongini, A.; Cardillo, G.; Mingardi, A.; Tomasini, C. Tetrahedron Asymmetry, 1996, 7, 1457
SECTION 74F:
Cyclopropanations, including Halocyclopropanations
y
1. “Cp2Zr”
o
r
E OEt
t
* , BFyOEt2
2.ph/\/CHo
Ito, H.; Kuro, H.; Ding, H.;
’
PhG
E
t
J. Am. Chem. SOC., 1998, 120, 6623.
2 eq Zn(CHzIh, CHzCh PhO -H
O
*
A>+”
P
h
v
O
H
MeN%888, MeN
98% (93% ee)
:harette.;Juteau, H.; Lebel, H.; Molinaro, C. J. Am. Chem. SOC.,1998, 120, 11942. w C 0 2 M e M e w
Me2CBr2, e-, DMF ,70°C TBAB ,TBAI
Leonel.,Paugam, J.P.; Condon-Gueugnot, S.; NedClec, J.-J.
CO2Me
60%
Tetrahedron, 1998, 54,3207.
Section 74F
91
Cyclopropanations
N2CHzCW t
A
Ph
A
*
bis-ferrocenyl bis-imine
Cho, D.-J.; Jeon, S A . ; Kim, H.-S.;
AL
Ph
*
&OH Ph 40%
Park, H.S.; Chung, S.H.; Kim. Y.H.SynLett, 1998, 1073. CHCl3 ,NaOH (powder) ,rt
X
S
e
TEBA-Cl
c1
C02Et
84% (64:36 trunsxis) - SynLett, 1998, 617.
SmI2,6 e~ HMPA
2.2
Br
Ph
P Cl
h 76%
Stefanl.;Petragnani, N.; Comasseto, J.V.; Braga, A.; Menezes, P.H. Synth. Commun., 1998, 28, 1667.
4
EtzZn, CH212
-p("
c@17
Ito, S.; Shinokubo, H.;
Tetrahedron Lett., 1998, 39, 5253.
Ph
6
Ph
82% (93:7 cis:truns)
C8H17
>"2
Ph
,pentme
Me02C
F
L
RhdS-TBSP)4
Ph
P
P h %0, COzMe
(97 86% ee Savies. H.M.L.; Rusiniak, L. Tetrahedron Lett, 1998, 39, 881 1.
i
+
&Ph *+*,
COzMe
3) 72%
Si(Oi-Pr),
Lee, J.;
MezN-CHO ,Ti(Oi-Pr)4 THF , -78°C J. Org. Chem., 1997, 62, 1584.
61% (1:2.2 a$)
92
Compendium of Organic Synthetic Methods, Vol 10
? i.l S
Section 74F
CpzTiCl2, BuLi ,THF -78OC -+it
Ph Ph Horikawa, Y.; Nomura,T.; Watanabe, M.; Fujiwara, T.; T J. Org. Chem., 1997, 62, 3678,
Cr(CO),
DMF , 4 % BHT ,152"C, 3(hnin
Fp = femocenyl
88% (97% de)
B a r l u e n u ; Femhdez-Acebes, A.; Trananco, A.A.; F16rez, J. J. Am. Chem. SOC., 1997, 119, 7591.
Me
SnBu3
4Ph BFyOEt2, toluene , -23°C
OCOzMe
:kt.
94% (>98:2 cixtrans) Sugawara, M.; Yosida..J. Am. Chem Soc., Z997, 119, 11986.
Ph-OH
MsHN
HN-S
0 1
EtzZn, CHzIz ,CHg12 -23"C, 20 h
P
h
O
quant (85% ee)
Imai.;Sakamoto, K.; Maeda, M.; Kouge, K.; Yoshizane, K.; &&miJ Tetrahedron Lett.. Z997. 38. 1423.
h
H
93
Cyclopropanations
Section 74F
-ph
PhCH=CH2 c h i R ~ ( I Icatalyst )
COze' N2
Davies.;Kong, N. Tetrahedron Lett., 1997, 38,4203. N2CHC02Ett rt , 2 h
*
LPh 0.15%Ru-porphyrin catalyst
60% (74 ee , IS,2S)
A
Ph
EtoZc
quant
(96:4 transxis)
Frauenkron, M.; B e r k e s s e u Tetrahedron Lett., 1997, 38, 7175. i-PrMgCl, CHzI2 PhO -H
*
Ph
35%
Bolm. C; Pupowicz, D. Tetrahedron IRtt., 1997, 38, 7349.
51% Chaplinski, V.; Winsel, H.; Kordes, M.; de Meiiere. A. SynLett, 1997, 111.
1 ,++*
N2CHC02r-Bu Co(1II)-den cat ph)
CHzCk
Ph
+
C@d-menthol
N2CHC02d-menthol DCE ,23"C
@ ,,,
Ph
p : l l l #-, %
*,*"
Ph
+ a
COZd-menthol
ph
COzt-Bu
5) 79% 51%ee
(82 60%ee Fukuda, T.; m k i . T, Tetrahedron, 1997, 53,7201.
ph)
98% 56% (98% regioselective ee ) Fernandez, E.; Hooper, M.W.; Knight, F.I.; Brown. J.M, Chem Commun., 1997, 173.
A
Ph
NsN=IPh , Rhz(OAc)4
Ns = N-@-toluenesulfony1)imino
2
s
e
Miiller, P.; Baud, C.; Jacquier, Y . Tetrahedron, 1996, 52, 1543.
85%
133
h i n e s from Mix.
Section 105
4
hcaMe NsONHCO$Zt, CH2Cb CaO
70%
C@Et Ns = (4-nitrobemenesulyl) Carducci, M.; Fioravanti, S.; Loreto, M.A.; PeUacani, L.; TardeUa, P A . Tetrahedron Len., 1996, 37, 3717.
SECTION 105:
AMINES FROM MISCELLANEOUS COMPOUNDS PhNH2, toluene, MS 4A
* PhvN‘Ph H Phe T O M e 5% Sc(OTf)3,16h nev. H,; Simcox, M.T.; Slawin, A.M.Z.; Giles, R.G. Sydett, 1998, 640. NHz-NMq, FeCl3.6 H2O pm3
*
P M 2
92%
82%
rt.30min I99% Tashiro, D.; Kawasaki, Y.; Sakaguchi, S.; Ishii, Y.J. Org. Chem., 1997, 62, 8141. PhCH20H Borah, R.; Deka, N.;
f OH
Ac@, mtI2, rt, 15 h
D PhCHzOAc J. Chem. SOC.(S), 1997, 110.
e- (2 F mol-') ,rt , 2 d , MS 4A
f
*
99%
CsH170H, 10% Cp2Sm(thf)z
toluene ,RT , 3 h * o'CH , 17 Ishii. Y,;Takeno, M.; Kawasaki, Y.; Muromachi, A.; Nishiyama, Y.; Sakaguchi, S. J. Org. Chem., 1996, 61,3088.
C7H15CHO15%Pd(PPh3)4 CO (5 a m ) , "FA, PhH 120°C, 18 h 81% Satoh, T.; Tsuda, T.; Kushino, Y.; Miura.;Nomura, M. J. Org. Chem, Z996,61,6476.
92%
El Ali, B.; Okuro, K.; Vasapollo, G.; Aluer. H.J. Am. Chem. Soc., Z996, 118,4264.
P h-
Me0
COzEt
10% Pd(OAc),, 20% NaOAc 35"C, HCOOH OH Me0
Trost.;Toste, F.D. J. Am. Chem. SOC.,1996, 118,6305.
0 69%
Esters from Aldehydes
Section 109
145
EtOH ,SiOz
*
CBH17O -H
C8H17\/\0 83%
Nascimento, M. de G.; Zanotto, S.P.; Scremin, M.; Synth. Commun., 1996, 26, 2715.
---
e- ,TEMPO modified-GF electrode (-)-sparkine
L
.r
Qo
OH 94% (98% ee) Yanagisawa, Y.; Kashiwagi, Y.; Kurashima, F.; Anazai, J.; Osa.;Bobbitt, J.M. Chem. Lett, 1996, 1043. Ac@ ,2 % TMSOTf 20°C , 2 min
PhMOH
*
PhM
O
A
c
quant -P.A.;Baugh, S.P.D.; Flack, S.S.; Inglis, G.G.A. Chem. Commun., 1996, 2625
SECTION 109: ESTERS FROM ALDEHYDES OSiEt3
QTBS
& CHo
ZnClz, CHzCIz, 25"C, 1 d *
Yang, H.W.; Romo.D.. Org. Chem., 1998, 63, 1344. PhCHO
1. HC(OMe)3 , Amberlyst-15 ,CHC13
2. cat BF3'0Et2, mcpba 3. DBU D e e . H,; Kim, J.Y. Tetrahedron Lett, 1998, 39, 1365.
69% (>19:1 transxis) 15.3 (syn:anti)94% ee
*
PhC02M e 95%
Compendium of Organic Synthetic Methods, Voi 10
146
Section 11I
MnOz , NaCN ,MeOH , 1 4 h LPhCOZMe PhCHO Lai. G,; Anderson, W.K. Synth. Commun., 1997, 27, 1281.
92%
MontrnorilloniteK-10 clay, rt
EtCHO
98%
AcZp ,0.2 h Zhang, Z.-H.; Li. T.4,; Fu, C . 4 . J. Chem. Res. (S), 1997, 174. MeOH, 3 eq Py
C 4 H v C H O
Cl-N
L-
OAc
C4Hg,COzMe
%iC1 )==O
b., c1
68%
0
G.A.; Bayne, C.D.; Donde, Y.; Tamashiro, G.S.; Hilberath, L.A. Synth. Commun., 1996, 26, 2633.
Related Methods: Section 117 (Ekters from Ketones)
SECTION 110:
ESTERS FROM ALKYLS, METHYLENES AND ARYLS
No examples of the reaction R-R + RC02R or RCO2R (R,R= alkyl, aryl, etc.) occur in the literature. For the reaction R-H + RC02R or RC@R, see Section 116 (Esters from Hydrides). NO ADDITIONAL EXAMPLES
SECTION 111: ESTERS FROM AMIDES
A
Ph
NEtz
1. Tf20, CHzC12, Py
-4O"C-+ 0°C
2. > 10 eq EtOH
Charette.;Chua, P. SynLett,
Kiessling, A.J.;
*
1998, 163.
Synth. Commun., 1997, 27, 923.
PhAOEt 94%
147
Esters from Esters
Section 113
1. MezNCH(OMe)2, DMF ,25"C
NH2
P h T o M e
.L
0 Anelli, P.L.; B
1
0
2. MeOH
m
A
;Palano, D.; Visigalli, M. Tetrahedron Lett., PhI(OAc)z, MeOH
*
"H2
Ph
94%
1997, 38, 2367.
Prakash.;Sharma, V.; Sadana, A. J. Chem. SOC.,(S),
PhO M 'e
40%
2996, 100.
Et 2. cyclohexanone
78%
C3H7 Wedler, C.; Kleiner, K.; Kunath, A.;
Liebigs Ann. Chem., Z996, 881.
SECTION 112: ESTERS FROM AMINES NO ADDITIONAL EXAMPLES
SECTION 113: ESTERS FROM ESTERS Conjugate reductions and conjugate alkylationsof unsaturated esters are found in Section 74 (Alkyls from Akenes). PhCHzOH ,toluene, heat
uOMe
Montmorillonite-PK10
Ponde, D.E.; -v.H.;Bulbule, V.J.; J. Org. Chem., 1998, 63, 1058.
MOAPh
; Gajare, A.S.
86%
148
Section 113
Compendium of Organic Synthetic Methods, Vol 10
i-PrOH, M 2 , 6 h
90%
Ph-C%Me Ph-co21-Pr Ranu. B.C,; Dutta, P.; Sarkar,A. J. Org. Chem.,1998, 63, 6027.
-%
1. cyclohexanone , SmI2 , 1% NiCl2
THF,rt,1 h
0
2. H30' Machrouhi, F.;
85%
Tetrahedron, 1998, 54, 11 111.
-
HOiw
1111111
P h y o M e
0
Ti(OEt),
KmkL Tetrahedron Lett.,
1998,39, 4223.
1. PhS(O)CH2Cl 2.KH
Ph
94~69%
0
3.t-BuLi * PhQo 4. H2SO4 Satoh. T,; Kurihra, T. Tetrahedron Lett., 1998, 39, 9215.
0
XYo
-
Matsuo, J.-i.;
Ph
CaEt
1. chual t i tetra~nin5LiBr TMTHF 2. PhCH2Br
*
P h-
63%(90%ee ,R) Tetrahedron Len, 1998, 39, 9723. ~-BuOAC, 1% t-BuOK, THF
w C O 2 t - B U
* Ph
Stanton, M.G.; hgnLM.& J. Urg. Chem, 1997,62, 8240.
88%
Section 114
Esters from Ethers
149
~ s ~ ( T M s ) ~
*
AIBN ,80DC
87%
;Ferreri, C.; Ballestri, M.; Curran, D.P. Tetrahedron Len., 2996, 37, 6387. ; Albeni, A.; Ballestri, M.; MacCiatelli, D.; Curran, D.P. Tetrahedron Lett., 2996, 37, 6391.
BuOH , S-Sn02, toluene heat, 6h
* M O B u Sap; Zubaidha, P.K.; Dantale, S.W.; Keshavaraja, A.; Ramaswamy, A.V.; Ravindranathan, T. Tetrahedron Lett., 2996, 37, 233.
-.
QAc -
OTBDMS
2eq
OMe
,DCE
97%
-
10%LiCo(B&2H11)2,1 d
ob
Grieco.;DuBay, W.J.; Todd,L.J. Tetrahedron Lett., 1996, 37, 8707. Me
' 8
Eu(fod)s ,CDCl3 ,rt
Shu Me ll.; Sakai, T.; SECTION 114:
J. Am. Chem. SOC., 80% 2996, 118, Me 11690.
ESTERS FROM ETHERS, EPOXIDES AND THIOETHERS
Or-Bu
2. TsOH ,CHC13
,THF
*
76~81% Tavlor.;Chmiel, N.H.; Mann, E.E.; Silver, M.E.; Vyvyan, J.R. Synthesis, 2998, 1009.
Compendium of Organic Synthetic Methods, Vol 10
150
Section 115
10% BiBr3,&, 110°C
DMF ,7.5 h Ph Chem. Commun., 1997, 95.
LeBoisselier, V.; Postel, M.;
do
MgO ,C02,400°C
/98% ee)
Also via: Section 27 (Acid Derivatives).
SECTION 118: ESTERS FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION 119: ESTERS FROM ALKENES
w
C3H7
Deng, L.X.;
A (CH&C02Me
MeSCH2CaEt
L
hv ,MeCN
n
C7H15 Tetrahedron Lett, 1997, 38, 7829.
Br
Cu powder, 130°C (CH&C02Me Metzeer. J.Q; Mahler, R.; Francke, G. Liebigs Ann. Chem.,1997, 2303.
78%
Compendium of Organic Synthetic Methods, Vol 10
156
Also via: Section 44 (Alcohols).
SECTION 120:
-
ESTERS FROM MISCELLANEOUS COMPOUNDS Pb$ BF4-, 2%Pd(0Ac)z
oms
Section 120
DME/H20, 30°C, 1 h
b
Pb
Karin.; Yamagucbi, T.; Ho, P.S.; Kim, W.-Y.; Yoon, S.-K. Tetrahedron k t t . . 1997. 38. 1947.
CeEt 87%
Compendium of’Ovganic Synthetic Methods Micheal B. Smith Copyright 02002 by John Wiley & Sons, Inc
CHAPTER 9 PREPARATION OF ETHERS, EPOXIDES AND THIOETHERS
SECTION 121:
ETHERS, EPOXIDES AND THIOETHERS FROM ALKYNES
PhOH , HSZ-360, PhCl 130°C, 6 h
40%
HSZ = a zeolite Bigi, F.; Carloni, S.; Maggi, R.; Muchetti, C.;
SECTION 122:
.
J. Org. Chem., 1997, 62, 7024.
ETHERS, EPOXIDES AND THIOETHERS FROM ACID DERIVATIVES NO ADDITIONAL EXAMPLES
SECTION 123:
a
ETHERS, EPOXIDES AND THIOETHERS FROM ALCOHOLS AND THIOLS cat Pd(dba)z ,air
/
80%
Larock. R.C.; Wei, L.; Hightower, T.R. SynLRtt, 1998, 522.
2 eq MeC(OMe), ,rt , 8 h
m O M e MontmorilloniteKSF 86% war.H.M.S,; Reddy, B.V.S.; Mohanty, P.K.;Yadav, J.S. Tetrahedron Lett., 1997, 38, 3619
O -H
~
Compendium of Organic Synthetic Methods, Vol 10
158
Me(CHdlgH2Br, BuLi THF mSH - O T + rt
Section 124
,
Yin, J.; -on.
98%
C, Tetrahedron Lett, 1997, 38, 5953.
f OH, Pd(0Ac)z PPh3 , Ti(Oi-Pr),, 1h
*no 90%
Satoh, T.; Ikeda, M.; Miura. M,; Nomura, M. J. Org. Chem., 1997, 62, 4877. Ph
Me0 Zhu, 2.; Espenson. J.H, J. Org. Chem., 1996, 61, 324. 1 . 1 2 , Mg
* ~~-0-Bn 82% 2. PhCH7Cl Lin.; Li, H.-H.; Zhou, A.-M. Tetrahedron Lett., 1996,37, 5159. Et-0-H
SECTION 124:
ETHERS, EPOXIDES AND THIOETHERS FROM ALDEHYDES
PhCHN2, PhCHO Cu(acac)~ Aggawal. V.K. SynLett, 1998, 329.
*
888t84,8
Ph
Ph
73% (>98:2 transxis) (93% ee ,RR)
Section 125
Ethers from Aucyls
NaH, TWF, -5"C, 1 d PhCHO
*
159
phiuittui
'"-p-
Mew, .0
0
0
63% (70% ee)
J. Chem. Soc., Perkin Trans. I , 1998, 3399.
Baird, C.P.;
Phfi-
NT~
PhCHO ,THF
Ph
* Bggarwal. V&
PhAPh
>98:2 trans:cis Calamai, S.; Ford, J.G. J. Chem. SOC., Perkin Trans. 1, 1997, 593.
PhCHO
M&oMe
*
PhCHN2, C U ( Z ~ C ) ~
ty
%, Ph
Ph
73% (93% ee,RR) >98:2 trans:cis Aggawal. V.K.; Ford, J.G.; Thompson, A.; Jones, R.V.H.; Standen, M.C.H. J. Am. Chem. SOC.,1996, 118, 7004.
PhCHO
C3H7'
N
.Ac
hv,MeCN, 14h
-19 p*, Ph
N
/AC
I
c3H7
(>90 B a c h . A n g e w . Chem. Int. Ed.,1996, 35, 884.
SECTION 125:
-b
Ph
%N/ Ac
I
c3H7
10) 70%
ETHERS, EPOXIDES AND THIOETHERS FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONAL EXAMPLES
Compendium of Organic Synthetic Methods, Vol 10
160
SECTION 126:
Section 129
ETHERS, EPOXIDES AND THIOETHERS FROM AMIDES NO ADDITIONAL EXAMPLES
SECTION 127:
ETHERS, EPOXIDES AND THIOETHERS FROM AMINES NO ADDITIONAL EXAMPLES
SECTION 128:
ETHERS, EPOXIDES AND THIOETHERS FROM ESTERS
dph
1. CpzTiC12 , PHMS ,THF 2. Et3SiH, CHK12, Amberlyst 15
90%
0
Hansen, M.C.; Verdaguer, X.; Buchwdd. S.L. J. Org. Chem, 1998,63,2360.
SECTION 129:
ETHERS, EPOXIDES AND THIOETHERS FROM ETHERS, EPOXIDES AND THIOETHERS PbCHzBr ,NaOH , PhCHO
"",,Il-~~
Julienne, K.;
aq MeCN ,rt
-
J. Org. Chem., 1998, 63, 4532.
Ph40
ph\\\*@
0.2 RuC13 , acetone reflux
*
Irannoor.;Kazemi, F. Synth. Commun., 1998, 28, 3189. NH4SCN, MeCN , 1 5 min
t
Ph
92% (88% trand84% ee ,SS)
)(ITph
TiO(tfa)z k a n m r . N,; Zeynizadeh, B. Synth. Commun., 1998, 28, 3913.
90%
Section 130
Ethers frm Halides
161
NHdSCN, Sic13
S
MeCN ,reflux
98%
- altnrk,Lz AIiyan, H. Synth. Commun.,1998, 28, 3943.
NH4SCN, 0.2 CAN, t-BuOH ,rt
/
50%
Rvan.;Stang, P.J. Tetrahedron Lett., 1997, 38, 5061. BuGnHpump, syringe , AIBN, reflux PhH
Chambournier, G.; Krishnamurthy, V.; &y&y.H.
t
j3:a 4:l 26%
Me Tetrahedron Lett., 1997, 38, 6313.
M e 3 , Ni(acach, THF , 0°C
with MeLi rather than AlMe3 Ichiyanagi, T.; Kuniyama, S.; Shirnizu, M.;
76% 0%
0% 99% Chem. Lett., 1997, 1149.
197
Ketones from Ketones
Section 177
T i C k Z n , THF, rt, 2 h
Phu / S . , P h
1
*
83%
Ph
Guo, H.; Ye, S.; Wang, J.; Z h g d . J. Chem. Res. (S), 1997, 114.
"-p
EtO-P EtO/
1. NaH ,RT 2. LiAlH4
Ph
*
3. H3O+
Tph 96%
0
Hong, J.E.; Shin, W.S.; Jang, W.P.; Oh. D.Y. J. Org. Chem., 1996, 61, 2199.
i,.
A/
C& ,Bu3SnH , AlBN PhH ,reflux, 4h
*
-a
.JL; Whitley, P.E. Tetrahedron k t t , 1996, 37, 559.
nh lm
3 pq TiC14/Sm/THF
S OzPh
Ph
Wang, J.;
rt,4h Synth. Commun., 1996, 26, 1931.
;K??;
0
~
Ph
ph + ph8*@* **4*848;kPh
Ph
m
65%
31) 95%
(69 Qkano. T,; Ohno, K.; Kiji, J. Chern. Lett., 2996, 1041. AIBN ,PhH ,BusSnH
I 0 &tenden. G .; Smithies, A.J.; Tapolczay, D.; Walter, D.S. J. Chem. SOC..Perkin Trans. 1. 1996. 7.
72% ( 2 1 rransxis)
0
Compendium of Organic Synthetic Methods, Vol 10
198
Section 179
REVIEW: "Conversion of the Thiocarbonyl Group Into the Carbonyl Group.'' Corsaro. Pistad, V. Tetrahedron, 1998, 54, 15027.
a;
Related Methods: Section 49 (Aldehydes from Aldehydes).
SECTION 178: KETONES FROM NITFULES NO ADDITIONAL EXAMPLES
SECTION 179: KETONES FROM ALKENES 0.003 Co(tpp) , 3 rt,2d Ph-
i-BuONO
3 eq Et3SiHt i-PrOH-CHzC12 67% Hamasuna, Y.; Matsushita, Y.-i. SynLett, 1998, 1270.
;-
OSiMe3
Fe(N0313, DMF
*
,lt+ 60°C ;-
-
7%
63-0 51%
Dainty, R.F. Tetrahedron Lett., 1998, 39, 5097. PhH ,bromo perfluorooctane
ph-
Betzemeier, B . ; Lhermitte, F.;
* A Ph
t-BuOOH
Tetrahedron Lett., 1998, 39, 6667.
PhCHO , 5 % RhCl(PPhi)3, To1 c
20% 2-amino-3-picolineI150"C, 1 d
m. C.-H,;
Lee, H.; Hong, J.-B. J. Org. Chem., 1997, 62, 1200.
72%
95%
Section 180
199
Ketones from Misc.
1. BHpTHF ,CH2C12
78%
2. PhH ,FCrO3, CH2C12 Parish. EJ,; Kizito, S.A.; Sun, H. J. Chem. Rex (S), 1997, 64.
see also: SECTION 180:
Section 134 (Ethers from Alkenes). Section 174 (Ketones from Ethers).
KETONES FROM MISCELLANEOUS COMPOUNDS
Conjugate reductions and reductive alkylations of enones are listed in Section 74 (Alkyls from Alkenes). 1. t-BuOK, THF 2. H20
c02et
3. 90% 4. aq NH4Cl Adam, W.; Makosza, M.; Saha-Moller, C.R.; Zhao. C . 4 , SynLett, 1998, 1335. wet NaBiO3-silica microwaves, 5 min
*
; De, A.; Karchaudhuri, N. SynLett, 1998, 1345.
K
r
NH4+ CrO3Cl-, alumina
(Jo
73%
A
* 85% 60"C,5h Ph zhano. (3.4.; Yang, D.-H.; Cben, M.-F.; Cai, K. Synth. Commun., 1998, 28, 2221. Ph
1
L 95% Clayfen , 6 h Clayfen = clay support NH$JO3 Ph Ph Meshram, H.M.; Reddy, G.S.; Srinivas, D.; yaday. J.S. Synth. Commun., 1998, 28, 2593.
Oxone, MeOH c (0 Na2HPODaOH Ceccherelli, P.; Curini, M.; Marcotullio. M.C; Epifano, F.; Rosati, 0. Synth. Commun., 1998, 28, 3057.
81%
200
Compendium of Organic Synthetic Methods, Vol 10
Section 180
74% zhanp. G.-L; Yang,D.-H.; Chen, M.-F. Synth. Commun., 1998, 28, 3721.
ph)==N-NMe2
MezS04, KzC%
97%
t
Ph heat.10h Ph m a d . &; Arifuddin, M.; Rao, N.V. Synth. Commun., 1998, 28: 3927. 90% Baruah, M.; Prajapati, D.; Sandhu. J.S. Synth. Commun., 1998, 28, 4157.
Clayfen, microwaves , 1 min
e ph>O 78% Ph Ph Meshram. H.M.; Srinivas, D.; Reddy, G.S.; Yadav, J.S. Synth. Commun., 1998, 38, 4401. ~~
TMACUAI203, CHKl2 t
38°C
ph)=N4H
-
p h k O
TMACC = M e w + C Q C I G.-S.; Yang, D.-H.; Chen, M.-F. Org. Prep. Proceed. Int., 1998, 301, 713.
1,
\byBn 1 2
MeCN ,reflux, 15 min
95%
HaiiDour.;Mohammadpoor-Baltork, I.; Kianfar, G. Bull. Chem. SOC. Jpn., 1998, 71, 2655.
QVPh
KMnOdAl203, microwaves
Ph
L.
o%ph Ph
Benhaliliba, H.; Derdour. A,; Bazureau, J.-P.; Texier-Boullet, T.; Hamelin. J, Tetrahedron Lett.. 1998. 39. 541.
83%
83%
Ketones from Misc.
Section 180
EtOWHCOOH
201
+
0
>
heat
PhNHNHCHO
90%
93%
Khasnobis, S. Synth. Commun., 1998, 28, 1361.
;-
PhZI' BF4-
PhB(OH)2, CO ,0.5%Pd(PPh3)4
* PJ P K2CO3 ,DME ,30 min Lim, K.-H.; Ho, P.-S.; Yoon, S.-K.; Son, H . 4 . Synth. Commun., 1998, 28, 1481.
88%
h
;-
MeCN ,reflux, 15 min
El6
95%
I&
Bn'@
Ha-iimur. A.R,; Mahboubghah, N. J. Chem. Res. (S), 1998, 122. hexamethylenetetramine-Br2
r
.
C C 4 , H@, rt 4 h
85%
Bandear.;Admane, S.B.; Jare, S.S. J. Chem. SOC. (S), 1998, 154. SiOflrO3, CHzClz, 45 sec
=.
( j
95%
Ph microwaves Ph Bendale, P.M.; Khadilkar, B.M. Tetrahedron Lett., 1998, 39, 5867. C
0
b
94%
ph)=o
CH2C12, rt , 15 min Chaudhari, S.S.; Akamanchi. K.G. Tetrahedron Lett., 1998, 39, 3209. Mn(OAc), , PhH ,reflux
*
a/
Demir. AS.; Tanyeli, C.; AItinel, E. Tetrahedron Letr., 1997, 38, 7267.
92%
202
Compendium of Organic Synthetic Methods, Vol 10
r
Section 180
wet NaIO4-SiO2, microwaves
=
1.5 sec Ph Varma.;Dahiya, R.; Saini, P.K.Tetrahedron k t t . , 1997, 38, 8819. Ph
Envirocat EPZG , aq acetone
P h O N N H T s
80%
0-hP
90%
80"C,4h
Ballini. R.; Bosica, G.; Maggi, R.; Sartori, G. S y n k t t , 1997, 795.
Base.; Srinivas, P. Synth. Commun., 1997, 27, 3835.
Zr sulfophenyl phosphonate aq acetone, reflux
.n . nl.;Rosati, 0 . ; Pisani, E.; Cu P
N
-
O
H
SynLett, Z996, 333.
NaB03.4 H f l ,AcOH
95%
D@ -
89%
95"C, 8 h Wrr_ar. B P , ; Shaikh, S.I.; Iyer, S. Synth. Commun., 1996, 26, 1163.
60%
-)=ae?0Tf TfO DCE,6h
0Me Nenajdenko, V.G.; Baramenok, I.L.; &&&yaJ&
0 2 , Cu ,TMEDA PY.28h Balogh-Hergovich, 8.;Kaizer, J.;
/
OMe Tetrahedron, Z996, 52, 12993.
*
Chem. Lett., 1996, 573.
71%
Section l8OA
Protection of Ketones
203
Das. N&; Sarangi, C.; Nanda, B.; Nay&, A.; Sharma, R.P. J. Chem. Res (S), 1996, 28.
phT phY Zn-'PA-DMF
I
*
rt,15min
Saikia, A.K.; Barua. N.C.; Sharma, R.P.; Ghosh, A.C. J. Chem. Res. (S), Z996, 124. aq NaOH ,MeCN ph)-N-NH2
'>o
+
92%
56%
Khurana. J.M, ; Singh, S.; Panda, A.K. J. Chem.Res. (S), 1996, 532.
)(
N-NMe2 Pd(OAc)2--SnC12, 1 d Ph Mino, T.; Hirota, T.;
*
90%
DMF-HzO Ph SynLett, 1996, 999.
REVIEW: "Aldehydes and Ketones." Lawrence, N.J. J. Chem. SOC., Perkin Trans. I , 1998, 1739.
SECTION 180A: PROTECTION OF KETONES 0
PhMgBr ,THF ,-22°C
+
Ph
A,,
93%
PB u3+ CT Ph Maeda.;Takahashi, K.; Ohmori, H. Tetrahedron, 1998,-54, 12233
x:
0
0
Ph DMSO-THF ,2Q min Bose. D.S.; Srinivas, P. SynLett, 1998, 977.
t
A,,
Ph
92%
204
Compendium of Organic Synthetic Methods, Vol 10
Section 180A
Jnaneshwara, G.K.; Barhate, N.B.; Sudalai, A.; Deshpande, V.H.; Wakharkar,R.D.; Gajare, A.S Shingare, M.S.; Sukumar, R. J. Chern. Soc., Perkin Trans. I , 1998, 965.
0
ph)=N-OH
p>o
L
94%
CHzClz ,rt , 15 min
DeVos. D.E,; Sels, B.F.; Reynaers, M.; Subba Rao, Y.V.; Jacobs, P.A. Tetrahedron LRtt., 1998, 39, 3221.
HxozH
MeCN , oxamide catalyst, t-BuCHO
Oz,rt,6h Ph Blay, G.; Ferniindez, I.; Formentin, P.; Tetrahedron Lett., 1998, 39, 3327.
0-o
*
A
87%
Ph . Rosellb, A.L.; Ruiz, R.;
MeOH ,MCM-41
*
89%
Tanaka, Y.; Sawamura, N.; Jwamoto, M. Tetrahedron Lett., Z998, 39, 9457.
0 3
CeC13.7 H@ , MeCN ,15% NaI
=
rt, 12h
0;. 85%
Marcantoni. E,; Nobili, F.; Bartoli. G; Bosco, M.; Sambri, L. J. Org. Chern., Z997, 62, 4183 3.5 FeC13-6 HzO
0.06 M CHC13, rt
Sen.; Roach, S.L.; Boggs, J.K.; Ewing, G.J.; Magrath, J. J. Org. Chern., 1997, 62, 6684 Fe(NO3)3/SiOz, hexane , 10 min
*
99% C7H Is Hirano. M. ; Ukawa, K.; Yakabe, S.; Morimoto. T, Org. Prep. Proceed. Int., 1997, 29, 480.
205
Protection of Ketones
Section 180A
MontmorilloniteK10, R CHzClz, 40 min
Gautier, E.C.L.; Graham, A.E.; McKillop, A.; Standen, S.P.; Tetrahedron Lett., 1997, 38, 1881.
Shi, X.-X.;Khanapure, S.P.;
'y,
Tetrahedron Lett., 1996, 37, 4331.
Oxone, wet A1203
c
ph)=o
%%
Me CHCI3,15 min Me Ceccherelli, P.; Curini. M,; Marcotullio, M.C.; Epifano, F.; Rosati, 0. SynLett, 1996, 767. See Section 362 (Ester-Alkene) for the formation of enol esters and Section 367 (Ether-Alkenes) for the formation of en01 ethers. Many of the methods in Section 60A (Protection of Aldehydes) are also applicable to ketones.
Compendium of’Ovganic Synthetic Methods Micheal B. Smith Copyright 02002 by John Wiley & Sons, Inc
CHAPTER 13 PREPARATION OF NITRILES
SECTION 181: NITRILES FROM ALKYNES NO ADDITIONALEXAMPLES
SECTION 182: NITRILES FROM ACID DERIVATIVES CO(MI92, H2NS03Ht A203
* PhCN microwaves , 10 min Juncai.;Bin, L.; Yang, L.; Chanchuan, L. Synth. Commun., 1996, 26, 4545. PhCOOH
SECTION 183: NITRILES FROM ALCOHOLS AND THIOLS
ocHo
NO ADDITIONALEXAMPLES
SECTION 184: NITRILES FROM ALDEHYDES
HCOOH , S i 0 2 , microwaves
~
NHzOH, HCl
Me0 Me0 Fene. J.-C. ; Liu, B.; Dai, L.; Bian, N.-S. Synth. Commun., 1998,28, 3765. 1. H2NNMe2
* PhCN 97% 2. MezS04, KzCQ K m A . A.; Arifuddin, M.; Rao, N.V. Synth. Commun., 1998, 28, 4507. PhCHO
88%
62%
Section 188
207
Nitriles from Esters
1. NHzOH , HCI/NEt3,8 h C P 17CHO
2. phthalic anhydride
C@17CN
80%
PhCN
77%
E -€A Lin, G.-J. Tetrahedron LRtt, 1998, 39, 4047. NH20HeHC1, peroxy monosulfate
PhCHO
4 2 0 3 ,microwaves, 7.5 min
*
Bose.; Narsaiah, A.V. Tetrahedron Lett., 1998, 39, 6533. SECTION 185:
NITRILES FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONALEXAMPLES
SECTION 186: NITRILES FROM AMIDES (COcl), ,DMSO 3 eq NEt3, -78°C
bu&&L
-
Heck, M.-P.; Wagner, A.;
90%
Tetrahedron Lett., 1997,38, 2099.
d,,,,
Ph
WCN
Ph
MeCN , RT ,reflux, 12 h + HC02H, (HCHO), ’
-CN Ph 85%
J. Org. Chem., 1996, 61, 6406.
SECTION 187: NITRILES FROM AMINES NaOCl ,EtOH ,rt , 15 min PhCHzNH2 Yamazaki, S. Synth. Commun., 1997, 27, 3559.
w
SECTION 188: NITRILES FROM ESTERS NO ADDITIONAL EXAMPLES
PhCN
92%
Compendium of Organic Synthetic Methods, Vol 10
208
SECTION 189:
Section 193
NITRILES FROM ETHERS, EPOXIDES AND THIOETHERS NO ADDITIONAL EXAMPLES
acN
SECTION 190: NITRILES FROM HALIDES AND SULFONATES 2 eq Zn(CN)2 ,4% Pd(PPh3)4 DMF , 120°C, 2 h
+
81%
OMe Kubota, H.; Pice. K L Tetrahedron Lett., 1998, 39, 2907. CllH23CH2Br
Li-CH2CNt THF , -78"C, 1 h
OMe
* CllH23CH2CH$N 79%
Dber. D.F.; Kong, S. J. Org. Chem., 1997, 62, 8575. OCN CH3(CHzhMgBr
CH3(07CN
THF,O"C, 10h Koo, J.S.; ~LJJ. Synth. Commun., 1996, 26, 3601.
SECTION 191: NITRILES FROM HYDRIDES NO ADDlTIONAL EXAMPLES
SECTION 192: NITRILES FROM KETONES NO ADDlTIONAL EXAMPLES
SECTION 193: NITRILES FROM NITRILES Conjugate reductions and Michael alkylations of alkene nitriles are found in Section 74D (Alkyls from Alkenes). NO ADDITIONAL EXAMPLES
97%
Nitriles from Misc.
Section 195
209
SECTION 194: NITRILES FROM ALKENES
phF
MeCN , hv ,benwphenone t-BuNH2
php-C 77%
+
Ph Ph i T.: Y u; Watanabe, M.;Kojima, R.; Tanabe, K.; Shima, K. Yama&t.& J. Org. Chem., 1996, 61, 6438.
SECTION 195:
NITRILES FROM MISCELLANEOUS COMPOUNDS
-I4"
t-BuMe2SiC1, imidazole
-
PhCN , heat DMF H ;Piiiero, L.; Ufret, L.; Algarin, W.; Morales, J. Synth. Commun., 1998, 28, 2807. Ph
DBU ,microwaves, 2 min PhCH=N4H * PhCN w i t h a . G.; Syamala, M. Synth. Commun., 1998, 28, 4577.
81%
92%
MeReO3, H202
MeCNIAcOHPy
= / d C N StankoviC, S.; Espenson. J.H, Chem. Comnun., 1998, 1579.
>X
Ph*N--NMez
,acetone, 3 min t
Ph-CN
90%
97%
ocN
Altamura, A,; DAccolti, L.; Detomaso, A.; Dinoi, A.; Fiorentino, M.; Fusco, C.; C,Synth. Commun., 1998, 39, 2009.
N%
t-BuNC , 3 eq BuN=C=O NEt3 , toluene, 2 h
*
m; Gacon, A. Tetrahedron Left., 1997, 38, 3391. /N4H
1. CH2C12, rt , 8 h ,
C8Hl 2. Sc(OTQ3 Fukuzama. S,; Yamaishi, Y.; Furuya, H.; Terao, K.; Iwasaki, F. Tetrahedron Lett.. 1997. 38. 7203.
58%
C 8 H I 7 CN
85%
210
Compendium of Organic Synthetic Methods, Vol 10
Section 195
H2S04/Si@ ,microwaves , 4 min e PhCH=N4H PhCN 76% Kumar. H.M.S.; Mohanty, P.K.; Kumar, M.S.; Yadav, J.S. Synrh. Commun., 1997, 27, 1327 SmI2, HMPA ,THF , -78°C
OPMB 50% 11% b e . H.-Y,; Pae, A.N.; Cho, Y.S.; Poh. H.Y.: Chune. B.Y, Chem. Commun., 1997, 821. NC
PMB = p-methoxybenzoyl
CN
Compendium of’Ovganic Synthetic Methods Micheal B. Smith Copyright 02002 by John Wiley & Sons, Inc
CHAPTER 14 PREPARATION OF ALKENES
SECTION 196: ALKENES FROM ALKYNES
Me
Z
SiMe3
1.9-BBN 2. Me3N-O 3. PhBr ,Pd(PPh3)4, NaOH
Me
87%
Soderauist. J.A.; Letin, G. Tetrahedron Lett., 1998, 39, 3989.
Ph@ ,cat NaOH , 3 h
78% OTBDMS OTBDMS Qvaska T.V.; Roark,J.L.; Shoemaker, C.M.; Bordner, J. Tetrahedron Lett, 1998, 39, 5705 Ph
=
C&u
1. PhMgBr ,cat MnCl~,lOO"C toluene, 8 h 2. H30'
Ph
66% Yorimitsu, H.; Tang, J.; Okada, K.; Shinokubo, H.; Qshima. K, Chem. Lett., 1998, 11.
212
Section 196
Compendium of Organic Synthetic Methods, Vol 10
NBz2
B z ~ N HDEAD, , PPh3 ,THF 5% PdC12(MeCN)2, To1
kPh
86%
B Z-N
Fujiwara, N.; yamamOt0.. J. Org. Chem., 1997, 62, 2318.
x
1. (q2-propene)Ti(Oi-Pr)2, -5O"C, 2 h
*
J. Am. Chem. SOC.,1997, 119, 11295.
Urabe, H.; Takeda, T.; Hideura, D.;
CH2=CH2 , CH2Cl2, rt , 4 5 h
OBz
C~~(PC~~)~RU=CHP~
Kinoshita, A.; Sakakibara, N.;
Do
62% J. Am. Chem. SOC.,1997, 119, 12388.
t-BuOH ,DMSO
1
microwaves
*
Do
92%
O2N 02N Moehmam. F.M,; Emami, R. Synth. Commun., 1997, 27, 4073. B
u
e
&Br
In, THF, rt
Panu. B.C.; Majee, A. Chem. Commun.,
86% 1997, 1225.
213
Alkenes from Alcohols
Section 198
CO2Me
I
hv ,xylene ,reflux 30 min
in benzene Cmciani, P.; Stammler, R.; Aubert, C.;
II
0% J. Org. Chem., 1996, 61, 2699.
'
Ph
3.
=
J. Org. Chem., Z996, 61, 6018.
H2, Ni$-BER ,MeOH
Et
O"C, lh
AEt Et
+
BER = borohydride exchange resin Choi, J.; Yoon. N.M. Tetrahedron Lett., 1996, 37, 1057.
Ph
92%
1. BuLi 2. BF,*OEt2
US.; Cho, C.M.; Yoon, Y.-Y. Et
1)
(3 93%
SnBu3
=
cat X l 4
*
quant.
+
Asao, N.; Matsukawa, Y.; yamamOt0. Y. Chem. Commun., 1996, 1513.
SECTION 197: ALKENES FROM ACID DERIVATIVES NO ADDITIONAL, EXAMPLES
SECTION 198: ALKENES FROM ALCOHOLS AND THIOLS Ph-OH
Ph.$=CHC02Et*BaMnO4,PhH , 2 h
Shuto, S.; Niizuma, S.;
J. Org. Chem., 1998, 63, 4489.
99%(En= 23)
87%
Hv
"h
1. Soclz ,NEt3
*
2. RuC13 ,NaIO4
Ph
3. P P h 3 , 1 ~rt,
P$
O
H
2%Cp*ReO3, PPh3, PhCl ,90"C
A
*
Ph
Ph
55 turnovers
Cook, G.K.; Andrews. M.A, J. Am. Chem. Soc., 1996, 118, 9448.
* / BnO = -
DEAD, -3O"C+PPh3, 23°CTHF BnO
85%
Ph
Jiug D.O.; Joo, Y.H.; Cho, D.H. Synth. Commun., 1998, 27, 2379. L
Section 199
Compendium of Organic Synthetic Methods, Vol 10
214
88%
-0.0.
B. Tetrahedron Lett., 1996, 37, 4841.
(COCl)2, DMSO ,NEt3
(40
Gleiter.;Herb, T.; Hofmann, J. SynLett, 1996, 987.
-
60) 68%
SECTION 199: ALKENES FROM ALDEHYDES
0
Br@
1. KHMDS t
Ph'O\--Ph
trans selective Lawrence. N.J. ; Beynek, H. SynLett, 1998,497. C12CHC02Me
PhCHO ,Zn/TMSCl THF
Pb
Ph
2. PhCHO
t
99%(97:3 E:Z)
Ph*C02Me 70%(E only)
Ishmo.; Mihara, M.; Nishihama, S.; Nishiguchi, I. Bull. Chem. SOC. Jpn., 1998, 71, 2669
Et02CCHN2, PPh3 ,DCE ,50"C , 4 h
PhCHO
215
Alkenes from Aldehydes
Section 199
m C 0 2 E t Ph
*
0.025 R~C12(PPh3)2
90% (97:3 E:Z)
Fuiimurs 0,;Honma, T. Tetrahedron Lett, 1998,39, 625. BF3eOEt2, THF , 0°C + rt
CllH23CHO
C~IH~~CH=CH~
m
85%
Matsubara.; Sugihara, M.; Utimoto, K. SynLett, 1998,313.
x
C02Et Br
Br
1 . 4 eq t-BuLi ,THF , -78°C -+ 0°C
*
2. 1.5 eq PhCHO 3. H3O+
phwBu C02H
73%(>99:1 E:Z) Shindo. M.; Sato, Y.; Shishido, K. Tetrahedron Lett., 1998,39, 4857.
1. LDA , PhCHgH2CHO 2. MgCl
,O \
3. BuLi
I
9 8 ~ 8 3 ~ 7 3(3:4 % E:Z)
Ph
Ph
u; Yamada,N.; Asano, T. Tetrahedron Lett, 1998,39, 6935. NH40AdAcOH MeN02, ultrasound
McNultv, J.; Steere, J.A.; Wolf, S. Tetrahedron Lett., 1998,39, 8013.
Compendium of Organic Synthetic Methods, Vol 10
216
Me
>;
M ee0 y J O
Section 199
* Me0
OMe Petasis. N . k ; Hu, Y.-H. J. Org. Chem., 1997, 62, 782.
OMe
88%
Ti(Oi-Pr)~Clz,THF (Me.LN)3P=CH2,23°C 0
Brody, M.S.; Williams, R.M.; Finn. M.G. J. Am Chem SOC.,1997, 119, 3429. 1% ReOC13(PPh3)2, P(OEt)3
PhCHO
NZCHCOzEt, THF ,23"C
*
m C O z E t Ph
-
90%(>20: 1 E:Z) Ledford, B.E.; Carreira. E.h.I, TetrahedronLett., 1997, 38, 8125. 1. PhMgBr
+
-
2.
OHC
NMez
4pph3 Br 3. CuBr*AgzC@
73% ( E only) CH=CHCH2Ph
Shen.;Yao, J. J. Org. Chem., 1996, 61, 8659. 1. SiOz, h e m e C3HSHO
2. Php-CHC02Me, 2h
*
C@SH=CHCOZMe
reaction time was 42 h without silica gel Patil. V.J.; Mavers, U. TefrahedronLett., 1996, 37, 1281.
87% (1090 Z:E)
217
Alkenes from Amines
Section 202
Sakai, M.; Saito, S.; Kanai, G.; Suzuki, A.; Miva-
0
CHO
Tetrahedron, 1996, 52, 915. Ph
Ph2P+CH2PhBrEtMgBr 79% (E-only)
Shen.;Yao, J. J. Chem. Rex (S), 1996, 394. Related Methods: Section 207 (Alkenes from Ketones).
SECTION 200:
ALKENES FROM ALKYLS, METHYLENES AND ARYLS
This section contains dehydrogenations to form alkenes and unsaturated ketones, esters and amides. It also includes the conversion of aromatic rings to alkenes. Reduction of aryls to dienes is found in Section 377 (Alkene-Alkene). Hydrogenation of aryls to alkanes and dehydrogenationsto form aryls are included in Section 74 ( W l s from Uenes).
NO ADDITIONAL EXAMPLES
SECTION 201: ALKENES FROM AMIDES Related Methods:
Section 65 (Alkyls from Alkyls). Section 74 (Alkyls from Alkenes).
NO ADDITIONAL EXAMPLES
SECTION 202: ALKENES FROM AMINES NO ADDITIONAL EXAMPLES
Compendium of Organic Synthetic Methods, Vol 10
218
Section 204
SECTION 203: ALKENES FROM ESTERS OAc
SiMe3
TiC14, C H g I 2 , 0°C I
Yachi, K.; Maeda, K.; Shinokubo, H.;
/P I
*CJIll C5H11
%
91% (97:3 E:Z) Tetrahedron Lett, 1997, 38, 5161.
u -x Bim, I
Brunel, Y.;
>99:1 cis:trans) J. Am. Chem. SOC.,1996, 118,2289.
Maruoka, K.; Oishi, M.;
il
Fe(N03)3, Si@ ,h e m e , 60°C PhHs“
Section 210
Me
*
Hivano.;Komiya, K.; Yakabe,S.;
85%
PhHS\Me
Org. Prep. Proceed. Int., Z996, 28, 705.
ii) P h N S \ r Mophad-
Ph
Ph
PPh3
90%
/7 Ph
Ph
; Ghaffarzadeh, M. Tetrahedron Lett., Z996, 37, 1855.
phF
Ph Okurna.
-
MeNHCHO ,microwaves (1 min)
(Se), ,BuLi
55% Ph
IL;Koda, G.; Okumura,, S.; Ohno, A. Chem. Len.,2996, 609.
Ph
Compendium of’Ovganic Synthetic Methods Micheal B. Smith Copyright 02002 by John Wiley & Sons, Inc
CHAPTER 15 PREPARATION OF OXIDES This chapter contains reactions which prepare the oxides of nitrogen, sulfur and selenium. Included are N-oxides, nitroso and nitro compounds, nitrile oxides, sulfoxides, selenoxides and sulfones. Oximes are considered to be amines and appear in those sections. F’reparation of sulfonic acid derivatives are found in Chapter Two and the preparation of sulfonates in Chapter Ten.
SECTION 211: OXIDES FROM ALKYNES NO ADDITIONAL EXAMPLES
SECTION 212: OXIDES FROM ACID DERIVATIVES PhCHZBr ,Zn , THF ,aq W C l
* PhS02CH2Ph 0°C , 3 h Sun, X.; Wang, L.; Zhane. Y.Synth. Commun., 1998, 28, 1785. PhSOzCl
gwo
SECTION 213: OXIDES FROM ALCOHOLS AND THIOLS NVSoZPh
LOH
’ phH CMBP, 120°C
* s
0
2
P
CMBP = cyanomethylenetributylphosphorane
h
Tsunoda.;Nagino, C.; Oguri, M.; It6, S. Tetrahedron Lett., 1996, 37, 2459. Tsunoda.Ozaki, F.; Shiiakata, N.; Tamaoka, Y.; Yamamoto, H.; 1 6 , S. Tetrahedron Lett., 1996, 37, 2463.
SECTION 214: OXIDES FROM ALDEHYDES NO ADDITIONAL EXAMPLES
99%
230
SECTION 215:
Compendium of Organic Synthetic Methods, Vol 10
Section 215
OXIDES FROM ALKYLS, METHYLENES AND ARYLS m03,AcZO
Fe+3p-zeolite >99% (o:m:p 25:3:72) Smith.;Musson, A.; De Boos, G.A. J. Org. Chem., 1998, 63, 8448.
No, 79% Smith, K.; Musson, A.; DeBoos, G.A. Chem. Commun., 1996, 469.
18%
vo(N03htrt CH;?Cl;!,6 min 9 9 % (35:241 o:m:p)
+ 19% 2,4-disubstituted Dove, M.F.A.; Manz, B.; Montgomery, J.; Pattenden.;Wood, S.A. J. Chem. SOC.,Perkin Trans. I , 1998, 1589. 10%Yb(OT03, 69% HNO3
DCE, 12h
*
@ NO2
51%0/41%p
Waller. F.J.: Barrett. A.G.M.; Braddock, D.C.; Ramprasad, D. Chem. Commun., 1997, 613.
55% (o:m:p = 40:99.9%ee)
Nakamura, M.; Hirai, A.; Sogi, M.; Nakamura.E..Am. Chem. Soc., 1998, 120, 5846. 1. [CH2=C=CHLi]Li+,ether -20°C -+ rt
PO
2. aq m4c1
-eel, 90%
w z a s . J.& Alvarez, L.X. Tetrahedron Len., 1998, 39, 3935. PhCHO
M e 3 A l T K H Na+ ,To1
THF,RT
*
ph7--H
93%
HO Joung, M.J.; Ahn, J.H.; Yoon, N.M. J. Org. Chem, 1996, 61, 4472.
H
,OB z d
3.6 eq EtzZn, 0.05 Pd(PPh3)4 PhCHO , 7 h
Tamaru.;Goto, S.; Tanaka,A.; Shimizu, M.; Kimura, M.
-
r
57%
Angew. Chem. Int. Ed., 1996, 35, 878.
SECTION 303: ALKYNE - ALDEHYDE
Ph-
1. BuLi, THF, -40°C 2.2eqDMF,-40°C+
rt
w PC -HO 97% 3.10%aq KH2PO4, MTBE ,50°C Joumet. M. : Cai. D.; DiMichele, L.M.; Larsen, R.D. Tetrahedron Lett, 1998, 39, 6427.
Section 309
Alkyne - Ketone
241
-
SECTION 304: ALKYNE AMIDE NO ADDITIONAL EXAMPLES
SECTION 305: ALKYNE - AMINE NO ADDITIONAL EXAMPLES
-
SECTION 306:ALKYNE ESTER NO ADDITIONAL EXAMPLES
SECTION 307:ALKYNE - ETHER, EPOXIDE, THIOETHER
Gong, J.;
m.P I ,
J. Am. Chem. SOC., 1996, 118, 4486.
rims
02N\
OMe
I
I(0Ach
Kida, M.; Sueda, T.; Goto, S.; Okuyama, T.; Q&hiJd.
Chem. Commun., 1996, 1933.
-
SECTION 308: ALKYNE HALIDE NO ADDITIONAL EXAMPLES
-
SECTION 309: ALKYNE KETONE
= Ph -
Ph2I' BF4-. 0.2%Pd(0Ac)z CO ,D W @ , rt, 30min
Ph-e
Ph
89%
g. S.-K.; Lim, K.-H.; Ho, P.-S.; Kim, W.-Y.Synthesis, Z997, 874.
242
Compendium Of Organic Synthetic Methods, Vol. 10
Section 31 1
Br
3. Pd(0) ,PhBr Ph A r c a d i . a r i n e l l i , F.; Pini, E.;
Ph
43%
Tetrahedron Lett, 1996, 37, 3387.
c1
Ph-
5% CuI, N E t 3 , a , 30h
(0%without CuI)
Choudhury, C.; Kundu. N.G. Tetrahedron Lett., 1996, 37, 7323.
83%
SECTION 310: ALKYNE - NITRILE NO ADDITIONAL EXAMPLES
SECTION 311: ALKYNE - ALKENE
C 6 H
1. Dibal 2. PhGCLi , ether, -78°C
1 7
3. VO(OEt)C12, ether, -78°C
e
GH13
*
\
80% J. Am. Chem. SOC.,1998, 120,5124.
Ishikawa, T.; Ogawa, A.;
i 2
e
MgCl
~
d .8e0NEt7
Ramiandrasoa, P.; Brkhon, B.; Thivet, A.; &mi. Tetrahedron Lett.. 1997. 38. 2447.
M,; Chaiez, G.
Ph
Acid - Alcohol
Section 313
243
1. C P W l Z
*
C6H13-Li 2.
-Jy ,-5"C
C&1+
64% (96:4 E:Z)
3. aq HCI c1 Tetrahedron Lett., 1997, 38, 4857.
Kasatkin, A.;
1. BuLi ,THF , -78°C 2. TMSCl ,-78°C -+ rt
SOzph Orita, A.; Yoshioka, N.;
3. B L i , -78°C * 4. PhCHO , -78°C -+ 0°C 5 . lOeqTMSzNLi, r t , 1h Chem. Lett., 1997, 1023.
L
P
h 88%
SECTION 312: CARBOXYLIC ACID - CARBOXYLIC ACID
NagO3, ultrasound
75%
OH Xing. D.TC, Cao, Y.H.; Evans, T.T.; Kabalka, G.W. Synth. Commun., 1996, 26, 4275. Also, with NaOCl and ultrasound; 87%. Zhang, C.J.; Fu, P.P.; Kabalka, G.W. Synth. Commun, 1997, 27, 1601. Also,with NaOCl and microwaves; 86%. -Q. D.T.C,; Zhang, C.J.; Haynie, B.C.; Fu, P.P.; K a b a b , G.W. Synth. Commun., 1997, 27, 3235. ~ X I Q .D.T.C.;
a
OSiMe3
titanium silicate (TS-1) 70% t-BuOOH ,reflux, 1d
72%
Raju, S.V.N.; Upadhya, T.T.; Ponrathnam. S . ;Daniel, T.; m a .4 Chem. Commun., 1996, 1969.
-
SECTION 313: CARBOXYLIC ACID ALCOHOL, THIOL
BuCOOH
1.2 eq (EtO)2P(0)CN ,THF NEt3, -20°C
*
2. H3O+ bH Mizuno, M.; Shioiri. T. Tetrahedron Lett., 1998, 39, 9209.
72%
244
Section 315
Compendium Of Organic Synthetic Methods, Vol. 10
Cl2H254
CO2H
a-oxidase (Pisum satinum), 0 2
w
C
~ C02H
eOH
TRIS-HCI , 4 7 h
H
~
quant (>99% ee ,R) Adam, W.; Boland, W.; Hartmann-Schreiex, J.; Humpf, H.-U.; Lazarus.;Saffert, A.; Saha-MOller, C.R.; Schreier, P. J. Am. Chem. SOC., 1998, 120, 11044.
a
1. IpcZBC1, NEt3 ,THF
9-- H
COzH 2. aq NaOH ;aq H+ * Phn C q Wane.;La, B.; Fortunak, J.M.; Meng, X.-J.; Kaballca, G.W. Tetrahedron Len, 1998, 39, 5501. Ph
1. PhN02, NaOH ,160"C
0
P
h
91% (96% ee) H
A
O
H
2. H3O+
48% Srinivasan, P.S.; Mahesh, R.; Rao, G.V.; Kalyanam. N, Synth. Commun., 1996, 26, 2161.
-
SECTION 314: CARBOXYLIC ACID ALDEHYDE NO ADDITIONALEXAMPLES
SECTION 315: CARBOXYLIC ACID - AMIDE
/o"
--
WCbZ
1. Bn02CNCl Na
BnO
2.@H%PHAL 3. TEMPO, NaOCl , KBr BnO NaHCO3,86"C Reddy, K.L; Sharpless. K. B, J. Am. Chem. SOC., 1998, 120, 1207.
PhCHO
1
Me
NH2
,CO,LiBr,NMP
PdBrd 2 eq PPh3, H2SO4,12OoC
*
/
86%
Acvc
92% Beller. M.;Ekkert, M.; Holla, E.W. J. Org. Chem., 1998, 63, 5658.
I
Ph
Acid - Ester
Section 317
245
B.
Bad(-)-sparteine
~
~- -
Park, Y.S.; &aU!,
'7- -
/&
J. Org. Chem., 1997, 62, 1574.
C02H
Ac-p ,H 2 0 , ultrasound
Anuradha, M.V.; Jbvindranath, B, Tetrahedron, Z997, 53, 1123.
SECTION 316: CARBOXYLIC ACID - AMINE
K2C03 ,CUC02H ,DMF Me
-
QQMe63% C&H
-.
I H
ri
PelWn.; Carrasco, R.; M&quez, T.; Mamposo, T. Tetrahedron Lett., 1997, 38, 5107. Related Methods:
Section 315 (Carboxylic Acid - Amide). Section 344 (Amide - Ester). Section 351 (Amine - Ester).
-
SECTION 317: CARBOXYLIC ACID ESTER
-Synth.
Commun., Z996, 26, 3859.
Compendium Of Organic Synthetic Methods, Vol. 10
246
Section 322
-
CARBOXYLIC ACID ETHER, EPOXIDE, THIOETHER
SECTION 318:
NO ADDITIONAL EXAMPLES
-
SECTION 319: CARBOXYLIC ACID HALIDE, SULFONATE
mC02H
NBS ,HzSO4,85"C
87%
CF3CqH, 16 h Br Zhang, L.H.; Duan, J.; Xu, Y.; Dolbier Jr., W.R. Tefruhedron Zkft., 2998, 39, 9621.
-
SECTION 320: CARBOXYLIC ACID KETONE
gr-
e- , C02, BuWF4-DMF, 5°C a@ :H 75% Tetrahedron Lett., 2998, 39, 1591.
Kamekawa, H.; Senboku, H.;
Also via: Section 360 (Ketone - Ester).
-
SECTION 321: CARBOXYLIC ACID NITRILE NO ADDITIONAL EXAMPLES
Also via:
Section 361 (Nitrile - Ester).
-
SECTION 322: CARBOXYLIC ACID ALKENE PhCHO
CH2(COOH)2 ,NH~OAC, microwaves 3 min
Kumar, H.M.S,; Subbareddy, B.V.; Anjaneyulu, S.; Yadav, J.S. Synth. Commun., 1998, 28, 3811.
*
PhCHXHC02H
98%
Alcohol - Alcohol
Section 323
Ph
=
241
1. NaHFe(C0)4, CHg12fMF 50°C Ph
2. CuC12-2 H 2 0 , acetone
D
&riasamv. M,; Radhakrishnan, U.; Ramesh Kumar, C.; Brunet, J.-J. Tetrahedron Lett., 1997, 38, 1623.
c"'"
phPp HOzC
PhCHO , Al2O3, rt
60%
70%
microwaves
C02H Kwon, P.-S.; Kim, Y.-M.; Kang, C.-J.; &on.
*
ph%cozH
COzH T.-W. Synth. Commun., 1997, 27, 4091.
PhCHO ,USY-zeolite
82%
'COzH PhH ,reflux, 6 h 'C02H WanP 0.L,; Ma, Y.D.; Zuo, B.J. Synrh. Commun., 1997, 27, 4107.
Also via:
Section 313 (Alcohol - Carboxylic Acids). Section 349 (Arnide - Alkene). Section 362 (Ester - Alkene). Section 376 (Nitrile - Alkene).
SECTION 323: ALCOHOL, THIOL - ALCOHOL, THIOL
PhCHO
Mn ,TMSCl ,5% CrCl3 THFDMF ,65"C
+
Svato$ A.; Poland. W. SynLett, 1998, 549. microencapsulated5% Os04
Hkph
Ph
OH
*
H20-acetone-MeCN, rt ,NMO , 1 2 h Nagayama, S.; Endo, M.; &&aya&A .
&&y.-.L;
J. Org. Chem., 1998, 63, 6094.
Gille, B.; Bellosta, V . J. Org. Chem., 1998, 63, 3141.
74% (38:62 d1:meso)
84%
248
CompendiumOf Organic Synthetic Methods, Vol. 10
A
Section 323
0.03 Cp2VCl2,2 eq Me3SiCl , THF 2 e q Z n , 20°C, 13 h CHO
89% (91:9 d1:meso) 1Jirao. T.; Asahara, M.; Muguruma, Y.; Ogawa, A. J. Org. Chem, 1998, 63, 2812.
2 PhCHO
Rieke Mn ,THF , rt Ph$
Ph OH
Rieke..Kim, ; S.-H. J. Org.
64%(63:37 d1:mso) Chem, 1998, 63, 5235.
46% (98:l cis:trans)
Hays, D.S.; &. G.C. J. Org. Chem., 1998, 63, 6375.
2%Co (salen) ,1.5 H 2 0 , THF
*
Br&OH
--
OH
4"C, I d Furrow, M.E.; Schaus, S.E.;
Cp2TiClz ,
93% (%% ee) J. Org. Chem., 1998, 63, 6776.
0 c1 c
PhCHO Mn,THF
er. A,; Bauer, D. Eur. J. Org. Chem., 1998, 2673.
Kf-
Ph
OH 75% (82:18 syn:anfi)
AlCOhOl - Alcohol
Section 323
2
Sm(Hg), THF, rt
PhCHO
*
249
Ph,&
67%
OH
Synth. Commun., 1998, 28, 3991.
Wang, L.;
Ph
Mg HzO 7
2 PhCHO
I 80% (59:41 three.-erythro) OH Zhang, W . X . ; Li C.-L J. Chem SOC., Perkin Trans. 1, 1998, 3131.
hph
polymer bound Cinchona alkaloid
*
Ph
oso4,NMO
OH 90% ee
h ? h r ~ Gerlach, L A. Eur. J. Org. Chem., 1998, 21.
P
h
I n , HzO , ultrasound C H
C
Ph
Ph
OH
L h , H.J.; Keum, G.; Kang, S.B.;Chung, B.Y.;
4
Ph
Ph
70% (5:3 dl:meso) Tetrahedron Lett.,1998, 39, 4367.
KMnO4, t-BuOH , H@ ,15 min
Ph
* &OH ultrasound P Varma. R.S.; Naicker, K.P. Tetrahedron Lett., 1998, 39, 7463.
2 PhCHO
Mn, AcOH, H20, rt
~
Ph4
P
80%
h
OH 74% (44:56 threo:erythro)
J,i C.-J,; Meng,
Y.;Yi, X.-H. J. Org. Chem., 1997, 62, 8632.
250
Compendium Of Organic Synthetic Methods, Vol. 10
Section 323
Sm, 12, MeOH, rt, 5 min Ph 71%
24% Negoro, N.; Yanada, K.; Fujita, T. Tetrahedron Lett., 1997, 38, 3271.
-R;.
1. LiC104,O"C 2.2,6-lutidme-BH3
0
Ph
Ph
with NaBHpHFMeOH Narayana, C.; Reddy, M.R.; Hair, M.; &&&a. PhCHO
3% EBTHITiC12, Zn ,MgBr2 * MesSiCl
Ph
2
(99 : 1) 89% (25 : 75) 92% G.W. Tetrahedron Lett., 1997, 38, 7705. OH +
titanium dichloride
Ph
~
~
w
t
t
OH ~ ~
s
(97
Ph
:
Gansauer. A, SynLett, 1997, 363.
%Ph
o
HO
EBTHITiC12 = racethylenebis(q5-tetrahydroindenyl)
Ph
H
silica impregnated bis-Cinchona alkaloid t-BuOOH , H20, K3Fe(CN)6-K2Cg 10°C, 25 h
e
3)
5 88%
Ph
Ph
OH
88% (>!39% ee ,SS) Sone. C.E.; Yang,J.W.; Ha, H.-J. Tetrahedron Asymmetry, 1997, 8, 841. SmI2, Me3SiC1, THF ,rt , 3 min
*
C6H1 Honda. T,; Katoh, M. Chem. Commun., 1997, 369.
OH 77%
Alcohol - Alcohol
Section 323
PhCHO 3% (CsH5)2TiC12, MqSiCl * Phq Zn ,MgBr2,O"C
25 1
P
h
r"
li", 14) 93%
(86
+
0
OH
CpzTiCl, THF , 6 h + cyclopentadiene
OH
+)
"*..,
OH OH
OH
Bn o
OBn
Ph
6H
OH
Gansiiuer, A. Chem. Commun., 1997, 457.
--
Ph
+
Bn o
(5
1) 84% T . L ; Dutta, S. J. Chem SOC., Perkin Trans. I , 1997, 1257.
-ortv.
1. Cp2Ti(thf)C1, aq THF ,-78°C 2. hydrolysis
PhCHO
*
Ph,&
Ph
OH
goMe qo
Barden, M.C.; &byaUJ.
6, K2C03 aq. t-BuOH HOIlU'S'
* O {H
-E.J.; Noe, M.C.; Tmg, A.Y. Tetrahedron Lett., 1996, 37, 1735. Tetrahedron Lett., 1996, 37, 1739. Noe,M.C.;
252
Compendium Of Organic Synthetic Methods, Vol. 10
$“o
smI2,TMs-cl,THF,rt
Ph Nomura, R.; Matsuno, T.; -1
*rj’
Ph 57 % Am. Chem. SOC., 1996, 118, 11666.
1) 65%
(200 Clerici, A.; Clerici, L.; ports. 0, Tetrahedron L ~ t t1996, , 37, 3035.
Pedragosa-Moreau, S.; Archlas, A.;
6
Section 323
20%(98% ee 1 9 2 s ) 48% (69% ee 1WR) Tetrahedron Len.,1996, 37, 3319.
polymer-bound Cinchona alkaloid
Ph
-
@HQ);?-q.-silica gel
i r t l / O H Ph
m.B.B.; Nandanan, E.; Bhushan, V. TetrahedronAvmmefry, 1996, 7, 2805. 0 ~ 0 4 THF ,
,binaphthyl diamine
Ph/*\\
t
L
O
95%
H
Ph Rosini, C.; Tanturli, R.; Pertici, P.; Also via:
.
83% (%% ee ,R) Tetrahedron Asymmetry, 1996, 7, 2971.
Section 327 (Alcohol - Ester).
Section 357 (Ester - Ester).
Alcohol - Amide
Section 325
253
-
SECTION 324: ALCOHOL, THIOL ALDEHYDE PhCHO .toluene. -78°C CHO 2.2eq
OH
* PhL
(--$
C
H
O
99%
Oh-A1
\
Ph
Saito, S.; Shiozawa, M.; Ito, M.; yamamoto.H,J.Am. Chem.Soc., 1998, 120, 813. EtCHO ,Tic14
PhCHO
NEt3 , CHzClz
CHO
* Ph
Ti(Oi-Pr)4 ,4d TMEDA ,-25°C
Et 72% (97:3 syn:anti)
C
H
O
I
Et
Mahrwald.; Costisella, B.; Gundogan, B. Synthesis, 1998, 262. PhCHO
L Ph
Smlz, HMPA , THF
p
b
61%(7:93 syn:anfi)
m
C
H
O
80%
HO Shiue, J.-S.; Lin, M.-H.; F a n -e s J. Org. Chem, 1997, 62, 4643. ECHO, TiCl4, TMEDA
PhCHO
*
Ph&CHO
toluene, -40°C
72%
Me I y f a b W A ~ Costisella, .; B.; Gundogan, B. Tetrahedron Lett., 1997, 38,4543. Related Methods:
Section 330 (Alcohol - Ketone).
-
SECTION 325: ALCOHOL, THIOL AMIDE
0 N
I
CO2Me
mcpba ,MeOH , NaHCO3 CH2a2, rt
Sugisaki, C.H.; Carroll, P.J.;
f i o I M e
80-904(1:2 cis:trans)
N
I
COzMe Tetrahedron Lett., 1998, 39, 3413.
254
Compendium Of Organic Synthetic Methods, Vol. 10
c
Section 325
c
Uo
2.2 eq sparteine pentane , -95°C
13%
Kawasaki, T.;
.
SynLett, Z998, 1429.
hv , CHElz
Ph Lindemann, U.; Reck, G.; Wulff-Molder, D.; NMe2
qme’ me2
1. PhCHO , Pd(PPh3)4
2. H3O+ Cl3SiH, rt , 4 5 h -
Tetrahedron, Z998,54, 2529.
H
H
~
Ph
R
,
,
,
Ph
(32
68) 87%
ISivooka S . 4 ; Shimizu, A.; Torii, S . Tetrahedron Lett., Z998,39,5237. i - W H O , SrnIZ, THF
*
-78”C, 0.5 h i-Pr
.&’”\
Nd:
*
92% (78%de)
Fukuzaw!; Tatsuzawa, M.; Hirano, K. Tetrahedron Lett., Z998,39,6899.
~
~
Section 326
Alcohol - Amine
02
255
1.NaH.W
88%
/
2. conc HCl
Ts
Littler, B.J.; w z b er. TJ Boddy, I.K.;Riordan, P.D. SynLett, 1997, 22.
Do N I
Me$%-
82% /
BF30OEt2, CH2C12 , -78°C -+ 0°C
k02Et -Gross,
I
C02Et E.K.M.; Jurka,J. Tetrahedron Lett,. 1996, 37, 3255.
-
i-PrFo 0
3eqSmIz
H%NHi-Pr
Tmvfi
HO
Me
NHi-Pr
+Hr$ Ho
(1:1.5 syn:anti)
NHC Pr
NHC Pr
be
Me
0 37% 0 18% Yamashita., Okuyama, K.; Kawasaki, I,; Ohta, S. Tetrahedron Let?., 1996, 37, 7755. 1. (i-pr2N)2Mg , THF, fi
\
2. PhCHO
SOzPh 93% 0.Y.:Yoshida, A.; Sakamoto, T. J. Chem. SOC., Perkin Trans. 1, 1996, 2331.
S02Ph
-
SECTION 326: ALCOHOL, THIOL AMINE BuSnH ,AIBN , PhH ,reflux
73% (18:l transxis) Tonno, J.; Hays, D.S.; Fu. G . c J. Org. Chem., 1998, 63, 201.
256
Section 326
Compendium Of Organic Synthetic Methods, Vol. 10
1. L i t cat ClOHg, THF, -78°C 2. PhCHO 45%
3. H20 t-Bu
HO
Tetrahedron, 1998, 54, 12007.
Alonso, E.; Ram&, D.J.;
PhNH2, Yb(OTfl3, R-BINOL toluene, MS 4A,Ph2NBn , -78°C 90% (80%ee)
HOU.X,-L.; WU,J.; Dai, L.-X.; Xia, L.-J.; Tang, M.-H. Tetrahedron Asymmetry, 1998, 9, 1747.
a, N\
1.
OMe
Jf
o+?h
H N O H & B(OMe)@HySMe2 THF ,reflux 2.2NHCl 3. Boc-C1 ,NaOH
-
+
hBOC
NHBOC 28) 89% 36% ee
(72 65% ee Masui.;Shioiri, T. Tetrahedron Lett., 1998, 39, 5193. EtzNH, 2 eq LiOTf ,MeCN 20 min
/Irtt/NEt2 Ph
s; Leroy, R. Tetrahedron Lett., 1996, 37, 7715.
Liu, C.; Hashimoto, Y.;
(2.8
go. K, Tetrahedron Lett., 1996, 37, 6177.
+
p
h
E
O
H
1)
98%
";ioH-780cH/9
Section 327
Alcohol - Ester
257
-
SECTION 327: ALCOHOL, THIOL ESTER
H
;O:0'
4
'
;OZMe
2% Buz-S,II-P s"- c1
0-SnBuzCl BUZ
Orita, A.; Mitsutome, A.; Otera. J, J. Org. Chem., 1998, 63, 2420. 0.5% [Ru@-cymene)Cl2]2,i - M H 2% ephedrine, 6% i - M K
UOE
50"C, 15 h
uOEt
85% (94% ee , S)
- ;Mortreux, A.; Bulliard, M. Everaere, K.; Tetrahedron Asymmetry, 1998, 9, 2971.
H4
CBn
C02Bn
2.3 eqCAN ,MeOH , 4 h
CqBn 0°C -+ rt COzBn U v Nair, . ; L.G.; Mathew, J. Tetrahedron Lett.,1998, 39, 2801. i-PrCHO ,Cp2zTH2
THF,RT
ji,.,OH
-Lo+
Umekawa, Y.; Sakaguchi, S.; Nishiuama, Y.; Ishii.
95%
Y.J. Org. Chem., 1997, 62, 3409.
PbCHO , ( B z O ) ~NH4CYMgC104 , Br-COzEt
- phT CO2Et
OH Bieber. L.W. ; Malvestiti, I.; Storch, E.C. J. Org. Chem., 1997, 62, 904.
1. BrJ
52%
,In,H20
* L C @ M 2 . 0 3 ,MeOH ,Na2SQ Ph Yi, X.-H.; Meng, Y.; C-J. Tetrahedron Lett., 1997, 38, 4731. PhCHO
60%
e
78~82%
Compendium Of Organic Synthetic Methods, Vol. 10
258
1.
OMe
ether
2% Ti binaphthyl catalyst
Ph*cHo
*
2.TFA,THF Singer, R.A.;
p -
&C02Me Ph 95%(98%ee)
Tetrahedron Lett,, 1997, 38, 927. 1. LDA 2. t-BuLi
Br
Section 327
0
3. PhCHO
69%
3hkLM. Tetrahedron Lett., 1997, 38, 4433. K
PhCHO
'' x EtO
PPh2
OEt
4
68%overall (98%ee) 2. t-BUOK Ph COzEt 2. AD-mix-a Kirschnine. A.; Drager, G.; Jung, A. Angew. Chem. Int. Ed., 1997, 36, 253. 'C02Et 1. (Bu3Sn)@, WH sealed tube, PhSiH3 EtOH ,AIBN ,80"C
+
*
2. TBAF
Hays, D.S.; Fu. G.C, J. Org. Chem., 1996, 61, 4.
(1.6
1)
PhCHO , cat. DABCO J C O Z P h
78%
rt,3h Ph
Perlmutter.;Puniani, E.; Westman, G. Tetrahedron Lett., 1996, 37, 1715.
71%
Alcohol - Ester
Section 327
(99
Mahrwald.; Costisella, B. Synthesis, 2996, 1087.
259
:
1) 63%
Saccharomyces cerevisiae
Medson, C.; Smallridee. A.J.;Trewhella, M.A. Tetrahedron Asymmetry, 2997, 8, 1049.
1. Pd(dba)z, 2 eq AsPh3
toluene, 50°C
OAc
2.100"C C02Et
Ahiko, T.-a,; Ishiyama, T.;
1.
Chem Lett, 2997, 811.
,TS-1 molecular sieve * Ph&C@Me THF,rt
PhCHO 2. H2O
Sasidharan, M.; Raju, S.V.N.;
Also via:
82%
85%
; Paul, V.; Kumar.. Chem. Lett., 2996, 129
Section 313 (Alcohol - Carboxylic Acid).
Compendium Of Organic Synthetic Methods, Vol. 10
260
-
ALCOHOL, THIOL ETHER, EPOXIDE, THIOETHER
SECTION 328:
OMe
Section 3;
PhCHO ,7% CrCl2,2.5Mn ,0.2NaI
3.2TMSCl ,THF , -30°C
OMe
OH -
-
* -hP OMe
88% (10.9:lanti:syn) Hudack Jr., R.A. J. Org. Chem., 1998, 63, 3524.
;-
M
Pr
cat Bu3SnCl/NaBH4
180"C, 1 d
g
OF 1) 72% Mayer, S.; Prandi.;Bamhaoud, T.; Bakkas, S.; Guillou, 0. Tetrahedron, 1998, 54,8753.
(15
C02Et
1-Cl
VhV
OH
excess SmI2 , cat NiI2
THF,rt,3h
70%
Molander. G.A. ; Sono, M. Tetrahedron, 1998, 54,9289. PhSH , 5 % Ti(Oi-Pr)4 ( d e n ) hexane
X.-1.; Dai, L.-X.; Xia, J.-J.; Tang, M.-H. Wu, J.; Tetrahedron Asymmetry, 1998, 9, 3431.
4
Ph ;-
93% (63% ee , lS,2S)
Ce(OTf)4, MeOH ,25"C,2 min PhL O Shekarriz, M.; Shiring, F. Synth. Commun., 1998, 28, 347.
H
92%
Alcohol - Ether
Section 328
PH
0/\/OH
*d
ethylene glycol, 100°C, 2 h cat Ru(pPh3)3C12
Ph Wang, D.;
Bu$ nS ePh
261
Ph Synth. Commun., 2998, 28, 507. 1. BF30OEt2, CHzClz ,n
2.
65%
86%
c 5 H ' y S e P h OH
C5H,,-qo
. . Nlshlvama.; Ohashi, H.; Itoh, K.; Son& N. Chem. Lett, 1998, 159. cat 12, CHg12, rt , 3 0 min
HO Kim, K.M.;Jeon, D.J.;
Synthesis, 1998, 835.
67%
MeLi ,-90°C
* Ph
74%
HO Baird. M.&;Huber, F.A.M. Tetrahedron LRtt., 1998, 39, 9081.
TS-1 , aq H@2, acetone HO
rt,18h
TS-1 = titanium silicate (70 Bhaumik, A,; Tatsumi, T. Chem. Commun., 1998, 463.
30) 80%
SnBu3
0
0.1 PbI2 ,0.2 HMPA
Shibata, I.; Fukuoka, S.; Yoshimura, N.; Matsuda, H.; Baba. J. Org. Chem., 1997, 62, 3790.
OH
quant
Compendium Of Organic Synthetic Methods, Vol. 10
262
.
Iida, T.; Yamamoto, N.; Sasai, H.;
Section 328
80% (97% ee) J. Am. Chem SOC., 1997,119, 4783.
14% Ni(cod)2, 24% R-BINAP Me slow addition of Dibal (syringe pump)
% 0 ( J
QMe =
Me
/
60°C,4h OH Me
OMe
83% (97% ee)
Lautens. It&; Rovis, T. J. Am Chem. SOC., 1997,119, 11090. 1. (CF$02)Re03, TFAA CH2Cl2,2O0C
*
2. NaOMe ,MeOH
OH
@OH
54%
McDonald. F.E,; Singhi, A.D. Tetrahedron Lett., 1997,38, 7683.
MnOI) salen catalyst, PhIO
JIl"
PhCl , -30°C. 65 h 59%
Miyafuji, A.; y;ltsuk i. T, SynLett, 1997,836.
CHC13,45"C, t-BuOOH ,MS %4A h
;/OH
Palombi, L.; Bonadies, F.; Scettri. A, Tetrahedron, 1997,53, 11369.
63%
Section 328
Alcohol - Ether
263
M"..,,
**.& 3
OcHZph
BY&
+LPh
[ BuLii-PrzNH/t-BuOK]
THF ,-50°C
Me
*Bu
OH 80% Bindi, S.; Pecchi, S.; Capperucci, A.; Degl'Innocenti,A.; Reginato, G. J. Org. Chem., 1996, 61,4466.
..
;-
phY-
Ph
phwp
MeReOflz02, CHK12
OH
OH
2h
97%(syn:anti. 2:l)
Tetrahedron Lett., 1996, 37, 2717.
Boehlow, T.R.;
w
9 O
Y
AIBN , BuGnC1, EtOH + NaBH4, reflux
'
(94 Mayer, S.; Prandi, J, TetrahedronLett., 1996, 37, 31 17.
PhCHO ,0.5% Yb(fod)3 CHzCI2, rt ,20 h
6) 72%
*
97% Ph
Miles.;Berreth, C.L.; Anderton, C.A. TetrahedronLett., 1996, 37, 7893.
A
FeClglSiO2, MeOH ,25"C
"?OH OMe
Ph ;-
Tarrim, T.; Movahedi, Z. Synthesis, 1996, 1473.
95 %
(i-Pr)zTiBHd ,CH2C12
-2O"C,rt
Ravikumar, K.S.;
(82 Terrahedron, 1996, 52, 9137.
18) 86%
3 -3
264
Compendium Of Organic Synthetic Methods, Vol. 10
OTBDMS
Section 329
TBDMSO
4.5AgOTf ,25"C
Br
Hayashi, N.; Hujiwara, K.;
0
(3.8 : Chem. Lett., 1996, 341.
3% Co(salen) ,NaOH NaBH4, air,EtOH 4O"C, 1 h
Bamhaoud, T.;
+
TBDMSO
THF/H20
1) 91%
o3c o F ununii
1) 80%
(7 Chem. Commun., 1996, 1229.
-
SECTION 329: ALCOHOL, THIOL HALIDE, SULFONATE
/do
Ph ;-
12, cat PPI ,rt, CH2C12
97%
Ph
PPI = 2-phenyl-2-(2-pyridyl)imidaZolidine Naeimi, H. SynLert, 1998, 1343. Geotrichum sp.38
PhL
LI
*
*
F
p &F Ph
Wei, Z.-L.; Li, Z.-Y.; Lin. G . 4 . Tetrahedron, 1998, 54, 13059.
80% (70% ee ,S)
SiC14,10% HMPA , -78°C CH2C12, 20 min
* L
O
Ph
(17
H
+-
p
h
L
C
1) 94%
l
Denmark.;Barsanti, P.A.; Wong, K.-T.; Stavenger, R.A. J. Org. Chem. 1998, 63, 2428
Alcohol - Halide
Section 329
265
A
Ph
PhL
I >95%
w; Massah, A.R.; Eshghi, H.; Niknam, K. J. Org. Chem, 1998,63,1455.
O3
(62:38 E:Z)
' N O E t
HO E
y
+E>
Oms
0.2
&?
N-BH , E N 0 2
(89 93%ee
A T :
:
11)
87%
Iseki. K.; Kuroki, Y.; Kobayashi, Y. SynLett, 1998,437.
,,ll~~~
0, 0%
MgBr2, B u W H 4
-
ether-CH2Cl2, rt , 2 h
P hTsN 48 7 f P h
HO
72%(87%ee)
Bailey, P.L.; Briggs, A.D.; J a c k s o n . , ,Pietruszka, J. J. Chem. SOC., Perkin Trans. I , 1998,3359.
PhCHO
1. CHI3 , SmI2,O"C 2. H30+
t
61%
l*hp
I Concell6n, J.M.; Bernad, P.L.; Perez-An&&, J.A. Tetrahedron Leg., 1998,39, 1409.
P h q o
TMSCl ,phosphaferrocene CH2C12, rt
~
Ph Garrett, C.E.; Fu. G.C, J. Org. Chem, 1997,62,4534.
PhG
P
c1
h
96%
Compendium Of Organic Synthetic Methods, Vol. 10
266
/ l ~ ~ ~ ~ ~02CCFj ~~ 74% (93% trans)
Aranyos, A.; Szabb, K.J.; Backvall. J.-E. J. Org. Chem., 1998, 63, 2523.
(82 Lamarque, L.; Mkou, A.; Brun. P. Tetrahedron, 1998, 54, 6497.
11) 70%
Section 358
Ester - Ether
303
bNo2
CO2Me
K2S208, H2SOmeOH ,80°C
M & e(
93%
Ballini. R,; Bosica, G. Tetrahedron, 1997, 53, 16131.
Also via Dicarboxylic Acids: Hydrox y -esters Diols
Section 312 (Carboxylic Acids - Carboxylic Acids) Section 327 (Alcohol - Ester) Section 323 (Alcohol - Alcohol)
mso2 msoy
-
SECTION 358: ESTER ETHER, EPOXIDE, THIOETHER PhCHO , CH2C12 , 4 d * Me
Me+
~SOIIIIIIII
mso
14 Kbar ,64"C
Me
Ph
Ph
(63 : 37) Bellassoued. M, ; Reboul, E.; Dumas. F. Tetrahedron Lett., 1997, 38, 5631.
85%
(PhIO), ,MeOH
Aoms
OEt Moriartv. R.M, ; Rani, N.; Condeiu, C.; Duncan, M.P.; Prakash. 0, Synth. Commun., 1997, 27, 3273.
OTBScat 0°C TBAF + rt,THF C02Me
65%
ph-(oMe
.r
Ph
CO2Me
-$+ r*"d
MdzC
M e w (1.2
:
Evans.;Garber, L.T. Tetrahedron Lett., 1996, 37, 2927.
1) 86%
Compendium of Organic Synthetic Methods, VoI 10
304
Section 359
-
SECTION 359: ESTER HALIDE, SULFONATE
HO HO
Homsi, F.;
-
-&
I+(COllidiW)2PF6CH2Ch
51%(66:34)
J. Org. Chem., 1998, 63, 5255. BEt3, H 2 0 , rt
77% 0
J. Org. Chem., 1998, 63, 8604.
Yorimitsu, H.; Nakamura, T.; Shinokubo, H.;
C# l&H=CH2, H 2 0 cat Et3B/02
87%
0 1
PhI(OAc)2, E t w r CHzClZ, rt , 2 h
Hashem, Md.A.; Jung, A.; Ries, M.;
*
aoA
. Symktt., 1998, 1351.
Nakamura, T.; Yorimitsu, H.; Shinokubo, H.;
D
+
O '% A Br C (14 SynLett., 1998, 195.
Suzuki, Y .; Matsushima, M.; Kodoman'. M. Chem. Lett., 1998, 319.
Br
1)
59%
Ester - Ketone
Section 360
305
92%
Y. Tetrahedron Len., 1998, 39,4559.
Tankgucbi, Y.; Tanbaka, S.;Kitamura, T.;
SECTION 360: ESTER - KETONE
C
COZEt
COzEt
1. d i d t-BuOK
69%
2. TsOH*HzO
COzEt
6
0
solvent free Dieckmann Toda. F,; Suzuki, Y.; Higa, S. J. Chem SOC.,Perkin Trans. 1, 1998, 3521.
0 1.EtzZn ,CHzIz , 0°C OMe
2.NH4Cl
* +OMe
Brogan, J . B . ; & & & x & &J. Org. Chem., 1997, 62, 6444.
81%
0
I
t-Bu
~ I W
Ph-
,Pd(dba)z ,PPh3
&O CO H ,TsOH , m e , lOO"C, 2 h
+
Ph +o,*+*8Q
0
88% Monteiro. A.L, ; Lando, V.R.; Gasparini, V. Synth. Commun., 1997, 27, 3605.
Cl$IzlMgBr-CuBr*2LiBr b
m,rt
O Y 80% CI CloHZl Babudri, F.; Fiandanese, V.; Marchese. G,;Punzi, A. Tetrahedron, 1996, 52, 13513.
t-Bu
306
Section 361
Compendium of Organic Synthetic Methods, Vol 10
,C02Me
94% de ,91% ee , RS) Zhu, J.; Kramps, L. Liebigs Ann. Chem., 1997, 1101.
m;
; -
HO
2.5) 54% (1 118, 2860. Elomari, S.; Barnes, C.L. J. Am. Chem. SOC.,1996,
Tf20, CH2Cl2 2,6-lutidine, -78°C
(2
Harmata. a; Jones, D.E. Tetrahedron Lett., 1996, 37, 783. TiC14, CHgl2 -40"C, 1 h
rn
*SePh 77 % (97:3 cis:trans)
m;Kawai, S.; Ueno, Y. SynLett., 1996, 539.
1) 59%
Compendium of Organic Synthetic Methods, Vol 10
316
R
n
l
Section 366
n
Nair. V.; Mathew, J.; Nair, L.G. Synth. Commun., 1996, 26, 4531. ply-L-leucine , H202, Hfl CWk?
I 60% (62% ee) Kroutil, W.; Lastema-Shchez, M.; Maddrell, S.J.; Mayon, P.; Morgan, P.; Roberts, S.M.; Thornton, S.R.; Todd, C.J.; Tiiter, M. J. Chem. Sac., Perkin Trans. I , 1996, 2837.
L
0 2 , Et2Zn ,toluene,
0°C , 3 h
Ph
Enders.;Zhu, J.; SECTION 366:
PhCHO
*& Ph
F % q
%% (>99% de; 85%ee)
NMe2
Raabe, G. Angew. Chem. Int. Ed., 1996, 35, 1725.
-
ETHER, EPOXIDE, THIOETHER NITRILE
Me3SiCN, 0.1 Ti(0V) salen complex
*
Jams
Ph
+,
%.,
86% ee
CN Tararov, V.I.; Hibbs, D.E.; Hursthouse, M.B.; Ikonnikov, N.S.; Malik, K.M.A.;Olrizu, C.; E&~QIL Y.N. Chem. Commun., 1998, 387. modified Mg-AI hydroralcite (heated to 450°C) JCN
MeOH Kumbhar, P.S.; Sanchez-Valente, J.; 20% Ti(Oi-Pr)4, Me3SiCN
t
MeQ\/\CN
quant
Chem. Commun., 1998, 1091.
Jc; 84%(6o%ee,s) 22% salen derivative P Belokon'.;Flego, M.; Ikonnikov, N.S.; Moscalenko, M.; North., Orizu, C.; Tararov, V Tasinazzo. M. J. Chem. SOC..Perkin Trans. I . 1997. 1293. PhCHO
3 11
Ether - Alkene
Section 367
o=.
TMSCN ,CH2C12, -78°C 1% TMSN(SO2F)2,30 min
Qur, H.; Kaur, G.;
94%
Synth. Commun., 1996, 26, 1925.
REVIEW: "Sulfoximine-Titanium Reagents in Enantioselective Trimethylsilylcyanationsof Aldehydes Bolm, C.; Miiller, P.; Hams, K. Actu Chem. Scad. B, 2996, 50, 305.
ETHER, EPOXIDE, THIOETHER - ALKENE
SECTION 367:
En01 ethers are found in this section as well as alkenyl ethers. 1. PhCHO ,cat Cr-den TBME ,-30°C 2. cat H+ 85% (87% ee)
OMe Schaus, S.E.; Brhalt, J.;
-
J&&%LE&
5 q
OH
b
P '4#*## h
.
qc&
J. Org. Chem., 1998, 63,403.
C8H1h
-
5% Pd(OAc)z, 5% PPh3, DMF B u a C l , 5 eq CsgO3 .80°C, 3 d
m o c k . R.6; He, Y.; Leong, W.W.; Han, X.;Refvik, M.D.; Zenner, J.M. J. Org. Chem., 1998, 63, 2154. e
O
c
1
&
2
1
5% NaHFe(C0)4, aq EtOH
*
~
o
88%
C
l
o
H
reflux ,30 min 96% (4258 E:Z)
m; Kong, S. J. Org. Chem., 1998, 63, 6745. sph
Sm12, CH212 +
. .
Kumshuna.;Nakata, D.; Goto, C.; Hioki, K.;
Y
S
P
h
SynLeft., 1998, 1366.
97%
2
1
318
Section 367
Compendiumof Organic Synthetic Methods, Vol 10
1. LDA , THF, TMSCl , -100°C 2. H3O+
aPh
3. HOCH2CC13, DIC ,DMAP * CHzClz, rt 4. RCM , R u C ~ ~ ( = C H P ~ ) ( P C ~ ~ ~ PhH ,60"C &O
CO2CH$2C13
84~69%
tandem Claisen rearrangement Burke. S.D.; Ng, R.A.; Momson, J.A.; Alberti, M.J. J. Org. Chem, 1998, 63, 3160.
5% Pd(OAc)z, 10% MeSO3H
76% (>97% cis) Itami, K.; Palmgren, A.;
-
Tetrahedron Lett., 1998, 39, 1223.
Gilbertson.;Hoge, G.S. Tetrahedron Lett., 1998, 39, 2075.
Ai@03,
cgo3
acetone,H20
*
H %
Aurrecoechea..;Solay, M. Tetrahedron, 1998, 54, 3851.
73% (4.6:l anti:syn)
319
Ether - Alkene
Section 367
PhzI+BF4-, KgO3 ,DMF
*
60°C, 3h
Ph
S.-&; Yamaguchi, T.; Pyun, S.-J.; Lee, Y.-T.; Baik, T . 4 . Tetrahedron Lett., 1998, 39, 2127.
JPh [MeOCH(SPh)dCpzTi(P(OEt)3)21
I Pi Ph Rahim, Md.A.; Taguchi, H.; Watanabe, M.; Fujiwara, T.; Takeda. T, Tetrahedron Lett., Z998, 39, 2153. ~~
63%
'TSph : fSE Bu
2 eq y
r
2
, THF
,THF,reflux,2h Bu = 3.1N NaOH Ph 84% (19:81 E:Z) Takeda.;Watanabe, M.; Nozaki, N.; Fujiwara, T. Chem. Lett., Z998, 115. Ph
.OMe
3!XI: 1 cis:trans)
Ether - Alkene
Section 367
321
autoclave (100 a m ) CO , 0 2 , MeOH , KI
F O H
Pdz,70°C, 15 h 7
8
%
Gabriele, B.; Salerno, G.; DePascali, F.; Scianb, G.T.; Costa, M.; Chiusoli, G.P. Tetrahedron Lett., 1997, 38, 6877.
1.1%C ~ ~ ( P C ~ & R U = C H P ~ CHzClz ,O.OZ M
+
*
2. PhCHO ,BFyOEt2 CHzC12, -78°C
Cassidy, J.H.; W
Ph
(92 n . S.P.; Stemp, G. SynLeft., 1997, 1411.
:
8) 9 5 ~ 7 3 %
Me3SiCl , KI ,DMF pet ether, NEt3
u.J.-W; Liu, B.-S.
a1 //
O H * Gabriele, B.;
80) 97%
(20 Synth. Commun.,1997, 27, 739. K2PdI4,2ODC,mat
*
87%
Chem. Commun., 1997, 1083.
P h M H ,PdCl2(PPb3)2, CuI DW,NEt3,60°C, 16h
+
DPh
77% OH undu. N G ; Pal, M.; Mahanty, J.S.; De,M. J. Chem. SOC.,Perkin Trans. I , 1997, 2815.
85&;(rs*Q$-
Section 367
Compendium of Organic Synthetic Methods, Vol10
322
+Q$
OH
80%
80%at rt
Wrien, S.; Vicente, B.G.; lXxr&uf. P a Cjlem. Commun., 1997,1405. PhCHO ,30% Sc(OW3, hexane ,rt
O H = Deflate = Derfluorooctane sulfonate Bull. Chem. Soc. Jpn., 1997, 70,1421. Hanamoto, T.; Sugimoto, Y.; Jin, Y.Z.;
no
oT
BEt3 PhGnH, PhH ,heat
*
y
o +
MdzC
COzMe
b
I
i”
o
Me0S 1)
(10
97%
Evans. PA.; Roseman, J.D. J. Org. Chem., 1996, 61, 2252. Me0g toluene, reflux , 2 h 10% Pdz(dba)s ,2O’?h P(Oi-Pr)3
H
*
w n s . M,; Ren, Y. J. Am. Chem. Soc., 1996, 118, 9597.
To1
@h
15%
Clark.;Rooke, S.; Sparey, T.J.;Taylor, P.C. Tetrahedron Lett., 1996, 37, 909.
Halide - Halide
Section 368
(2
323
:
1) 69%
’>
Howell.;Fan, R.; TrUOng, A. Tetrahedron Lett., 1996, 37, 8651. Ph
=
PhSeAl(i-Bu)z , toluene
85% reflux, 1 d PhSe Dabdo&ub,; Cassol, T.M.; Batista, A.C.F. Tetrahedron Len., 1996, 37, 9005. +
qPh 1. CpgClz-Mg, THF ,0°C
88%
(fph
2. H2SO4
Miura, K.; Funatsu, M.; Saito, H.; Ito, H.; J-Iosomi. A. Tetrahedron Len., 1996, 37, 9059. Section BOA (Protection of Ketones)
Related Methods:
SECTION 368:
-
HALIDE, SULFONATE HALIDE, SULFONATE
Halocyclopropanationsare found in Section 74F (Allryls from U e n e s ) .
c 10H214
p-TolIF2, Et3N-5 HF ,CH2C12
tI,(, 65% -78°C -+ 0°C ClOH21 Hara. S.; Nakahigashi, J.; Ishi-i, K.; Sawaguchi, M.; Sakai, H.; Fukuhara, T.; Yoneda. N. SynLett., 1998, 495.
w
Ph
1 . 0 2 , 2 eq MnCl2 , 8 eq LiOMe , MeOH
2. conc HCl
* P
h
L
C
l
67% Hojo, M.; Murakami, C.; Ohno, K.; Kuboyama, J.; Nakamura, S.-Y.; Ito, H.; €bmLA Heterocycles, 1998, 47, 97.
-
w
CSHl 1
NaClO2, Mn(acach, CHzClz moist Al2O3, 20°C, 4 h
ph
Section 369
* C5Hll
Cl
80%
Synth. Commun., 1998, 28, 1871.
Yakabe, S.;
Ph
+
Compendium of Organic Synthetic Methods, Vol 10
324
1. BnNEt3' MnCk-, TMSCl ,CH2C12 ~
2. NaS2O3
4 Ph
P
c1 95%
Markb. 1.E,; Richardson, P.R.;Bailey, M.; Maeuire. A.R,; Coughlan, N. Tetrahedron Lett., 1997, 38, 2339.
SECTION 369:
HALIDE, SULFONATE - KETONE NaC102, Mn(acac)3, CH2C12 moist Al2O3,2OoC
Yakabe, S.; Hirano. M.: Morimoto. T. Synth. Commun., 1998, 28, 131. CuO ,MeSO$, MeCN reflux ,14 h
ra =ems
OMS
Lee.;Choi, Y. Tetrahedron Lett., 1998, 39, 3171.
h
71%
,20% 1ncl3
rt,30min
Diwu..; Beachdel, C.; Klaubert, D.H. Tetral.:dron Letf., 1998, 39, 4987.
67%
6-
Halide - Nitrile
Section 370
325
CAN, AcOWH~O,50°C
.
.
-&
94%
.; Kiji, S. Bull. Chem SOC. Jpn., 1997, 70, 421. 1. NaCl 2. Oxone
I
i
I2
I
3. NEt3 , CH2C12
c1 70%
r R K.; Nice, L.E.; Velu, S.E. Tetrahedron Lett., 1996, 37, 2377.
0-0
u (BFd-h
F-NZN-OH
MeCN m 8OOC, 8 h
*
$.
80%
Stavber. S,; Zupan, M. Tetrahedron LRtt., 1996, 37, 3591.
Kohrlj, J.; Ko?evar, M.; Polanc. S. Synth. Commun., 1996, 27, 3583.
SECTION 370:
-
HALIDE, SULFONATE NITRILE
DAST
*
DAST = diethylaminosulfonyltrifluyoride
&CN
Kirihara, M.; Niimi, K.; Momose. T, Chem. Commun., 1997, 599.
77%
326
Compendium of Organic Synthetic Methods, VoI 10
HALIDE, SULFONATE - ALKENE
SECTION 371:
C 6 H lC S H
Section 372
Brh
NaB03.4 H@ ,NaBr , AcOH
*
Br
c6H13
G.W; Yang, K.Synth. Commun., 1998, 28, 3807.
2.5 eq LiBr ,2.5 eq benzoquinone
90%
(17:83 E:Z)
Bu&;3%
BuL AcOH , 5 % Pd(OAc)2, rt * Backvall. J.-E,; Jonasson, C. Tetrahedron LRft., 1997, 38, 291.
-
SECTION 372:
KETONE KETONE TMS
Ph
Me
Crane, S.N.; Burnell. D.J. J. Org. Chem., 1998, 63, 1352.
J. Am. Chem. SOC., 1998, 120, 4015.
Matsumoto, S.; Okubo, Y.;
Cahrera.;Rosas, N.; Sharma, P.; LeLagadec, R.; Velasco, L.; Salm6n, M.
p;r-
Synth. Commun., 1998, 28, 1103.
Fe(NO3)3*1.5NzO4, EtOAc 2.5 h
Ph
IruiIzl-
0
.
*
4fPh
Ph
0
Pant
; Zolfigol, M.A. Bull. Chem. SOC.Jpn., 1998, 71, 905.
Ketone - Ketone
Section 372
327
0 Yasuda, M.; Tsuji, S.; Shibata, I.;
J. Org. Chem., 1997, 62, 8282.
>99%
y
0.3
1.
OMS
Gunawardena, G.U.; Arif, A.M.;
h
v
B
r
ii
82% Tetrahedron Lett., 1997, 38, 7603.
AcCl ,SmI2, MeCN
*
"fl
83%
0
0
+. Bn
b
60% J. Am. Chem. SOC.,1997, 119, 2066.
Baruah, B.; Boruah, A.; Prajapati, D.;
P
t
2. 3. aq NEt3, AcOH hat
0
Ying, T.; Bao, W.; SY.; Xu, W. Tetrahedron Lett., 1996, 37, 3885.
PhOCl , Sm12 70°C , MeCN
Hao, W.; ;-
uph 78%
Ph Ying, T.; Lu, P. Synth. Commun., 1996, 26, 2421.
328
Compendium of Organic Synthetic Methods, Vol 10
SECTION 373:
Section 374
-
KETONE NITRILE
Bakers yeast, MeCHO PhL
;-.
C
N
petrol, HzO
* P
h
k
71%
Ten, A.; Trewhella, M.A. Tetrahedron Lett., 1998, 39, 5121.
Shirnizu. I.; Fujita, M.; Nakajima, T.; Sato, T. SynLett., 1997, 887.
SECTION 374:
89%
KETONE-ALKENE
For the oxidation of allylic alcohols to alkene ketones, see Section 168 (Ketones from Alcohols and Phenols) For the oxidation of allylic methylene groups (CkC-CH2 Section 170 (Ketones from Alkyls and Methylenes).
-+
C=C-C=O), see
For the alkylation of alkene ketones, also see Section 177 (Ketones from Ketones) and for conjugate alkylations see Section 74E (Alkyls form Alkenes).
1. FVP (550°C)
2. H30+
=
&
Liu, H.; Shook, C.A.; Jamison, J.A.; Thiruvazhi, M.; Cohen. T, J. Am. Chem. SOC.,1998, 120, 605.
0
/
Ph Jwasawa. N,; Matsuo, T.; Iwamoto, M.; Ikeno, T. J. Am. Chem. SOC., 1998, 120, 3903.
89%
Ketone - Alkene
Section 374
329
Pp e OEt -OH
'OEt
Pd(OAc)2, THF ,NazCQ
-Y.;
+ v
Arisha, A.H.I. J. Org. Chem, 1998, 63, 5640. 1. BuLi ,THF ,-78°C 2.ZnCl2, THF ,-78°C + rt
* Ph\
3. PhCOCl , 5 % Pd(PPh3)4 80%
Y.-Zk; Mo. X . 4 , Tetrahedron Lett., 1998, 39, 1945.
rph co cat [RhCl(C0),]2,
Bu@ , 130"C, 18 h Koga, Y.; Kobayashi, T.; &r&&&
* O &
89%
Chem Lett., 1998, 249.
do CPh 1. Cp2TiC13 ,Mg , THF ,0°C 2. BTC
*
bme2 *@ BTC = bis-(trichlorornethyl)carbonate
Zhao, Z.; Dine. Y. J. Chem. SOC., Perkin Trans. I , 1998, 171.
75%
BuMgCl ,CeC13
BU
75%
Fonenas, C.; AkhWu-H
:.
Balavoine, G.G.A. Synth. Commun., 1998, 28, 1743.
cat 0 2 , PhH , cat Si02 80°C
v; Beni, Y.A. J. Chem. Res. (S), 1998, 138.
330
Compendium of Organic Synthetic Methods, Vol 10
Section 374
hv ,LiC104
45% photoinduced electron transfer
Fagnoni, M.; Schmoldt, P.; Kirschberg, T.;
Tetrahedron, 2998, 54, 6427.
, 5 % CpRu(PPhd2Cl
Ph-
6%Nd'Frj, Py ,100"c
Ph
@
8 13%
2. 1. H30' T i c k , -78"C, 15 min
I
83%
. . m; Fang, J. Tetrahedron Lett., 1998, 39, 8381.
.O
1% Hg(C104h MeCN , H20 TBDMSO
0 -
Hashmi..;Schwarz, L; Bolte, M. Tetrahedron Lett., 2998, 39, 8969.
\
84%
Section 374
Ketone - Alkene
G
Finlay, J.; ;-
~ e a - H z 0 2CH2C12 ,
*
331
0
97% Meh03 0 0 Gunarame, H.Q.N. Tetrahedron Lett., Z998,39,5651.
Okuro, K.; AIDer. H, J. Org. Chem., 1997,62,1566.
Kokubo, K.; Matsumasa, K.; Miura.
Murakami. M,; Itami,K.; Ph
i_
m, Nomura, M. J. Org. Chem., Z997,62,4564.
J. Am. Chem SOC.,Z997,119, 2950.
WeLi, ZnC1-J ,0°C 5% N i ( d ) z , THF
82%
Montoeomerv.; Oblinger, E.; Savchenko, A.V. J. Am. Chem.SOC.,1997,119, 4911.
Compendium of Organic Synthetic Methods, Vol 10
332
Ru3(C0)12, DMF ,140"C 15 a m CO, 20 h C07Me
Mag'
II
6
Y
74%
CoZMe
1. MeMn(C0)s 2. hv ,ether
*
78~58%
Tetrahedron Lett., 2997, 38, 1781.
Lee, J.E.; Hong, S.H.;
TSiMe2Ph
P
. J. Am. Chem. Soc., 1997, 119, 6187.
Kondo, T.; Suzuki, N.; Okada, T.;
md '
Section 374
*
NMO , CH2C12 ,THF
1. 2.LDA ,THF , -30°C *
qo
B.-C,; Hong, J.-H. Tetrahedron Lett., 1997, 38, 255.
96%
Ketone - Alkene
Section 374
OSiMe3
(PhIO),-MesSiOTf
*
SiMe3
Monartv.,Epa, W.R.; &a&LQ.
a
333
52%
J. Chem Res (S), 1997, 262.
PhH ,reflux , 1 2 h
H
84%
W/
Bigbv.;Rege, S .D.: Sandanayaka, V.P.; Kirova, M. J. Org. Chem., 1996, 61, 042.
1.
Ph
Ph
DMF , 110°C ,24h , (i-R)3SiCN 2. H30'
Zhang, M.; &&mU&L
Eta
2W nm) ,MeCN ,0.04M
5% Pd(PW3)4, NEt4Cl 2 NaSOzPh, DMF -
-&
,CO ,50°C
SO2Ph
61% Brown, S.; Sridharan, V.; Uttley, M.D. Tetrahedron Lett., 1997, 38, 5031.
&gg&;
7=
phY
MeS02C1, [R~Clz(PPhj)d PhCl , 120°C, 6 h
Ph
SOzMe
*
0
86%
m; Udodaira, K.; Shimizu, T. J. Chem. Soc., Perkin Trans. I , 1997,783. EtO, EtOy
0
1. TMSCl ,NEt3, toluene
II
C02H
p
2. PhCOCl ,MgC12, rt
v
0
0
*
E t O - b A EtO'
Ph
92% Kim. D.Y.; Kong, M.S.; Lee, K. J. Chem. SOC.,Perkin Trans. 1, 1997, 1361.
Rathore, R.; Kochi. J.K. J. Org. Chem., 1996, 61, 627. EN&, Amberlyst-A(L7
0
4h
-YY NO2
0
05ph+
. . Balhnl.; Marziali, P.; Mozzicafreddo, A. J. Org. Chem., 1996, 61, 3209.
TBsY Ph
TolSOfla ,MeOH 2 eq Mn(pi43 0°C
76%
leZ3fh
Tolog
Tolw
14% 74% Mochizuki, T.; Hayakawa, S.; khawka. K, Bull. Chem.SOC.Jpn., 1996, 69, 2317.
Oxides- Alkenes
Section 389
347
1. MgCl2 ,NEt3 ,PhCOCl 2. cat p-TsOH ,H@ ,reflux
IJOEt
EtO'f EtO
IJ
EtO/r EtO
88%
Kim.;Kong, M.S.; Kim, T.H. Synth. Commun., 2996, 26, 2487. SECTION 388:
Ph
-
OXIDES NITRILES NO ADDlTIONAL EXAMPLES
SECTION 389:
-
OXIDES ALKENES
89%(99% ee) (99:l endo:em) Evans. D.A,; Johnson, J.S. J. Am. Chem. SOC.,1998, 120, 4895.
8
HY-zeolite ,N O , CCl4
0"
75OC, 2 h * Sreekumar. R.; Padmakumar, R.; Rugmini, P. Tetrahedron Lett., 2998, 39, 2695.
78%
G-
Anbazhagan, M.; Kumaran, G.; Sasidharan, M. J. Chem. Res. (S), 2997,336. SnBq
AIBN , PhH ,reflux, 2 h
Giardink A.; Giovannini, R.;
SO2Ph
Tetrahedron Lett., 2997, 38, 1995.
85%
Section 390
Compendium of Organic Synthetic Methods, Vol 10
348
0
McClure.;Herzog, K.J.;Bruch, M.D. Tetrahedron Lett., 1996,37, 2153. 1. LDA , THF , -78°C
1) 85%
SOzMe
2. DMF, MeI, rt, 1"C, 1 d
40% (>201 E:Z)
Dishington, A.P.; Mucciioli, A.B.; SjmDkins. N.S. SynLett., 1996,27. MeN02, Envirocat EPZG , lOO"C, 20 min
c&13CHO
-
C& &H=CHN02 94% ( E only)
M.B.; Wadgaonkar, P.P. SynLett., 1996, 149.
-Zirange,
0
1. BuLi , -78°C
* xs@c:O% (78:22 Z:E) Lee, Y.S.; Ryu, E.K.; Yun, K.-Y.; KhnJll, SynLett., 1996,241. 0 S2
2. H20, NCS ,0°C
SECTION 390:
-
OXIDES OXIDES NO ADDITIONALEXAMPLES
Compendium of’Ovganic Synthetic Methods Micheal B. Smith Copyright 02002 by John Wiley & Sons, Inc
Author Index
Abdo, T. Abe, H. Abe, N. &ib&QA
4Iuim.K Adams, N.D. Adibi, M. Admane, S.B. Ager, D.J. al. V.K.
Agnelli, F. Agrios, K.A. Ahiko, T.-a. b a n , J. Ahmar, M. Ahn, C. Ahn, J.H.
AhnJa
Ahn, S . 4 . Ahn, Y . 4 .
Ai&x
Aihara, H. Aires-deSousa, J. Aitken.R.b Ait-Haddou. H. Kit-Mohand, S. Aizpurua, J.M. Akashi, M. Akazume, M. Akiba, M. Akila, S. Akiyama, H. Akiyama, R. Akiyama, Y. Albert, R. Alberti, A.
Alberti, M.J. Alcaraz, L. Alexander, C.W. Algarin, W.
AuYLH.
Aliyan, H.
283 114 061, 341 019 223 169, 199, 231, 244,270,272 240 037 201 130 025, 094, 158, 159, 168, 307 151 113,295 259 130 332 098 136,240 190 017 292 113 166 292 239 329 186 110 186,201 294 345 141 046 072 29 1 022,297 109 068, 076, 239, 242 283 125, 149 318 339 029,087, 290 112 209 231, 232,233 161
Alizadeb, A.-A. Allen, J.G. Aller, E. Alonso, D.A. Alonso, E. Alonso, F. Alonso-Alija, C.
LibaJL
Altamura, A. Altinel, E. Alvarez, L.X. Alvisi, C. Amador, P. Amin, SK.R. Anastasia, L. Anazai, J. Anbazhagan, M. Anderson, W .K. Anderson. P.G. Anderton, C.A. Ando, A. Ando, T.
Aixbm&u
Anelli, P.L. Angeles, E. Angell, R.M. Anjaneyulu, S. Annunziata, R. Ansari, M.A. Anson, M.S. Antenori, M. Antonelli, E. Anmdha, M.V. AnzaiM. Aoki, K. Aoki, M. Aoki, Y. Aoyagi, S. ,4ovama T, Apodam, R. Aponick, A. Ar-Xing, W. Arai, N.
AniA
Arai, T. Araki, F. Araki. S, Araki. T.
349
295 073 293 034, 114 256,274 058,074, 185 034 110, 143, 144 288,288, 307 310,331 209 201 240 037 018 125 183 145 347 146 034, 114, 122 152 263 185 114 214 147 192 002 246 116 186 076 081 010 245 185 070 168, 185 095 015 185 273 266 036 336 314,345 313, 314, 345 180 096,266, 276 116, 117
Compendium of Organic Synthetic Methods, Vol 10
350
Aranyos, A.
AuadiA
Archlas, A. Ariente, C. Arienti, A. Arif, A.M. Arifuddii, M. Arimoto, K. Arimura, K. Arisawa, M. Arisha, A.H.I. Arista, L.
Arizo,
x.
Armnestad. B. Armstrong 111, J.D.
L!LmmuA Amould. J.C, ,4rterburn. J.B, Asahara, M. Asai, S. Asakawa, K. Asano, T. Asao, N. Aspinall, H.C. Ahnani, A. Attenni, B.
AluJ
Aubert, C. Audergon, L.
AlluLL
Aujard, I. Aurell, M.J. ,4urrecoechea. J.M. Avedissian, H. Avery, M.A.
Baba, K.
I#huLuL Babu, B.S. Babudri, F.
BadlL
302 242 252 271 299 327 200,206 069,081 086, 117 184,287 329 186 116 343 161 165 012 169, 234 248 069, 340 268 030 215 019,213, 339 152 022 174 281 113, 116, 295 213 087 256 290 084 274, 318 075,076 131
013, 023, 038, 060, 083, 119, 121, 261, 327 2% 276 041 305 028, 159
Bachki, A.
Jla!zuL
Backvall, J.-E.
Badone. D. Baeton, H. Bahzad, D. Baidossi, W. Baik, T . 4 .
€!a&x
Bailey, M. Bailey, P.L. Baird, C.P.
Bajpai, A.R. Bak, R.R. Baker, S.R. Bakkas, S.
J2d&LLM
Bak6, P. Bakstad, E. Balaji, B.S. Balalaie, S. K .Balaux, 8 Balavoine, G.G.A. Balduzzi, S. Balenkova E.S. Ballestri, M. Balogh-Hergovich, 8.
IiabkuL
Bamhaoud, T. Bandear. B.P, Banerii. A. Bank. B.K. B a n d , P. Bao, W. Baquer, S.M. Baraznenok, I.L. Barbier, F.
lhmLQ
Barden, M.C. Bardot, V. Barf, G.A. Bargues, V. Barhate. N.B.
Authors
029 286 074, 302, 318 326 098 131 173 039 319 135 324 265 159 261 061 082 103, 104 260 343 086 005 306 294 041,046 151 329 042 082,202 149 055, 082, 202, 271, 303, 346 202 054 260,264 044,055, 201, 202,348 178 137, 188 171 301, 313, 327, 335 114 114 082,202 166 052, 126 251 277 168 221 204
Author Index
B3rhWLL
Barmore, R.M. Barnes, C.L. Barnhart, R.W. Baroni, M.
u Barsanti, P.A. Bartoletti, L.
lbm!i& IiamduW J3UasL Baruah, B.
Baruah, M. Basu, M.K. Batista, A.C.F. Batsanov, A. Baud, C. Bauer, D. Baugh, S.P.D. Bayne, C.D. Bayston, D.J. BZWIZ~U,J.-P. Beachdel, C.
kakL Jbxk&EE liw&xdu BfzhLLL
E&LL Ikkkuma
Belanger, D.B.
l?dLedL
Bellosta, V.
l&&kLx& Belotti, D . Benaglia, M. Benbrook, D.M. Bendale, P.M. Benhaliliba, H. Beni, Y.A. Bennett. G.D.
092, 125 131, 132 315 187
098 002, 102, 141, 230 264 320 039,204 028, 126, 177, 178, 233 203 054, 190, 290, 327, 335 066,084, 135, 136,200 277 113 323 191 132 248 145 106,146 320 200 324 107, 108, 245 137, 188 114 042 166,232 169 050 285
001
303 129,244 308 124, 247 316 316 124 116 010 201 200 329 020
Berger, S. Bergmann, K.E. B&illon, L. Berkessel. A, Berlin. K.D, Bemaw, P. Bemabeu, M.C. Bemad, P.L. Bernardelli, P. Bemth, C.L. Besemer, A.C. Besev, M.
lkmumAL
Singh, A.P.; Mi Betzemeier, B . Betzemeier, B . Beynck, H. Bezodis, P. Bhaduri. A.P, Bhalerao, U.T. Bhar, S. BharaWi, B . Bhatt, R.K. Bhauacharyya, S. Bhaumik. A, Bhindenvala, N.S. Bhushan, V. Biagetti, M. Bian, N.-S.
Bietlot, E. Bigi, F. Bigot, A. Billotte. S, Bin, L. Bindhu, K.H. Bindi, S. Bindu, K.H. Birckbichler, P.J. Blackstock, S.C. Blackwell, H.E. Blake, A.J. Blanc, D.
l3mmAL Blay, G. Blechert. S,
351
088 119 076 093 067 010 288 289 265 309 263 050 104 0.; Balaji, B.S 286 068 198 214 175 173,295 044
032 313 089 097, 131,293 261 112 252 308 206
019 257 338 157,299, 335 041 103 206 184 263 140 010
190 227 191 035 013 011,082, 106 204,221
108
352
Compendium of Organic Synthetic Methods, Vol 10
JuuULL IiQiLUx Bobbitt, J.M. Boddy, I.K. Boden, D.J.
Boehlow, T.R. Boggio, C. Boggs, J.K. Bohnert, C.J. Poland. W. Bolitt, V. B!d€LLL
Bonadies, F. Bongini, A. Bonnet-Delpon, D. Booker-Milburn. K.I. Borah, R. Borate, H.B. Bordner, J. Bordoni, M. Boruah, A. Bosch, E. Boscia, G. Bosco, M.
Ibd2.S.
Bosica, G. Bosnich. B, Bosref, J. Boudiouk. P. Bougauchi, M. Bouzbouz, S. Bouzide, A. Bowden, M.C. Bower, S. Boyd, J. Boys, M.L. Braddock, D.C. Braga, A.
BlaaAL
Brhalt, J. Brandt, T.A.
039 073 145 255 227 260 263 124 204 232 244,247
002
016, 018, 093, 154, 167, 249, 317,330 186,234, 262 090 026 166,232 198 055, 143 056 211 055 054, 066,084, 135, 136, 190, 290, 327, 335 235 082 039, 204 114, 138, 202, 203, 207, 237 055, 202, 303 021, 187 038 080, 176 313, 314 192 041, 042, 106 271 017
050
233 107 002, 102, 141, 230 091 139 317 311
Brayer, J.-L. Bdhon, B. Brenner, E. Breuning, M. Brielmann, H.L. Briggs, A.D.
Brocksom, T.J. Brocksom. U. Brody, M.S. Brogan, J.B. Brook. M.A, Brookhart. M. Brown, C.W.
lirQmJx
Brown, S. Brown, S.M. Bruch, M.D. Bruness. L.E, Brummond. K.M, Brun. P, Bruneau. C. Brunel, J.-M. Brunel, Y. Brunet. J.-J, Brunner, H. BruMer, M. Bryann, V.J. Bnezinski, L J . Buchwald. S.L.
Buck, R.T. Bugl, M. Bulbule, V.J. Bulliard, M. Bumanin. N.A,
lhlQw&
Burk. M.J, Burke. S.D, Burkhardt. Burnell. D.J. Burton. D.J. Burton, J.
l.lms&A
Busch, S. Buston. J.E.H.
Authors
098,099 242 123 015 287 265 015 138 147 218 218 216 305 042 125, 187 010 132 346 017, 046,047 348 255 005,223 302 224,279, 299 014, 235, 297 218 181,247 026 143 184 310 134, 050, 123. 128, 129, 130. 153, 160, 162. 196, 333, 334 099,293 225 147 257 001,067 014,297 073 318 034 326 239 087 289 309 122
353
Author Index
Busujima, T. Butcher, T.S.
l3JmumL
102, 267, 270, 295 219 096,266,276
Cassol, T.M. Castailo, A.M. Castellano, G. Castet-Caillabet,D. Casy, G. Cave, A. Caycho, J.R.
c2izaJA
CaiA Cai, K.
calamai,s.
m u e l o . J.M. Cant, F. Cannon, A. Cantel, R.-M. Cao, G . 4 . Cao, P. Cao, R. Cao, Y.H. NCCl. A, Cardamone, R. Cardillo, G. Cardom, L. Carducci, M. Carloni, S. Carlsen, P. Carney, J.R. Caroline, J. Carran, J. Carrasco, R.
Carreilo. M.C. Carroll, P.J. Casadei, M A . Casamtbios, L. cases, M. Casolari, s. Cassidy, J.H.
240 326 012 024, 038, 039, 068, 075, 076, 078, 193 240 04,048, 199 065, 112, 151 101 159 120 031,040 125 334 125 268, 272 034 016 243 263, 320 098 090 011,082, 106 133 157 027 223 046
257 005 245
014. 019, 108, 216; 258,284 172 253 110, 143 125 281 037 321
Ceccherelli, P. Cerreti, A. Cesare, V.
-
alaJX
!aaLs.
Chabanis, 0. Chaiez, G. Chakrabarti, D.
clamhua Chakrabofty, R.
Chamboumier, G. Champagne, P.
manAsc
c2bLmKL Chm, T.-H. Chanchuan, L.
5JlauuK
Chandwadkar,A.JH. Chang, F.-J. Chang, N.-Y. Chang, S.K. ChaO, D.-Y. Chaoleur. Y, Chaplinski, V. Chapman, E.
LJEmBum
Charnsangavej.C. Charoenying, P. Chatani, N. Chatterjee, A. Chaudhari, B.A. Chaudhari, K. Chaudhati, S.S.
cbamLms ciu!mAE
323
064
152 075 073 174 037 271,332 199,205,237 28 1 172 043,091,096 190 013 332 242 127 201 031,040 251 196 052 015,016 107, 122 065,184,286 206 114 131,263 013, 043, 045, 116, 143, 187 008 279 072 102 336 218 093,097 278 090, 096, 103, 126, 146, 220 095 279 307,336 149 293 186 008 201 173 011, 149
354
Compendium of Organic Synthetic Methods, Vol 10
Chelle, F. ChelK-Regnaut, I. afa&
!2hwJL
Chen, C.-D. Chen, D. Chen, G. Chen, H.G. Chen, J. Chen, K.-J. Chen, L. Chen, M.-F. Chen, P. Chen, W.-x. Chen, Y. Chen, 2.-C. Cheng, C.-L.
-
Cheng, R.-Y. Cheon, H.G. Chhabra, B.R. Chhatriwalla, A. Chieffi, A. Chin, S.-F. Chinchilla, R. Chiocconi, A.A. Chitnavis, A. Chiusoli, G.P. Chmiel, N.H.
c!%KL
Cho, C.M. Cho, C.-G. Cho, C.-W. Cho, D.H. Cho, D.-J. Cho, H.-S. Cho, I.S. Cho, S.H. Cho, Y.S. Choi, H.-S. Choi, J. Choi. J.H. Choi, J.S. Choi, J.-K. Choi, S.-B. Choi, S.-C. Choi, W.-K. Choi, Y. Choi, Y.J.
046,094 320 046,047 038 049 193 060,300 153 102 231 142 191 046, 048, 199, 200 115,280 298 224 234 0566
094
292 127 050 020 088 270 289 127 049 321 149 014 213 022 190 178, 179,214
091
015 029
140
210 018 074, 088, 213 022 102
127 080 098, 338 126 140,270, 324 345
Choplin, A. ch2dlAL
C h o u m . B.M. Choudhary, R.K. Choudhary, V.R. Choudhury, C. Choueiry, D. Chowdhury, A.R. Christie, R. Christoffers. L Chua, P. Chun, Y.S. Chum. B.Y. Chung, B.Y. Chung, E.-A. Chung, S.H. Chung, S.-K. Chung. Y.K, Ciliberti, L. w n i . M.
aadLU
Clark, B.P. Clark, J.H, Clayton, T.C. Clerici, A. Clerici, L. Cli, Y. Clive. D.L.J,
€QbLx
Coi. P.G, Coldham. I.
Colins, C.C. Colombier, D. Colonna, S.
Combes, S. Comina, P.J. Comins, D.L. Compain, P. ConcelMn, J.M. Condeiu, C. Condon-Gueugnot, S . Constantieux, T. Cook, G.K. Coop, A. Corev. E.J, Corral, J.
, -C
Corrette, C.P.
Authors
309 225 186, 313 308 077, 134 242 183 295 017 085,087 103, 146 014 029,210 249 190 091 311 332,334 267 116 322 298 228,233, 235 085 054,252, 272 252,272 036 067 035, 328 017 122, 124, 125, 292 167 332 236 088,091 122 192 284 139 265 303 090 297 214 138 154,251 152 253 076
355
Author hdex
198 301 106, 124.192, 247,281 037 Costa, A.L. 321 Costa, M. 041,202 Costantino, U. 253, 259 Costisella, B . 324 Coughlan, N. 177 Coutts, I.G.C. 038 Couty, F. Covarrubias-ZBfiiga. A, 071, 307 289 Cowden, C. 116 Cozzi. F. 186 !&gJL 326 Crane, S.N. 079 iklsdzL 317 0. J.V. 167 Cronin, M.F. 029,044 i2.mAKQ 125 213 Cruciani, P. 075 chbaDAL 209,270 ihuxid. 041, 199, 202, 205,237 032, 108, 149, Curran. D.P. 312 022 CZS, M.-Z.
-
Dalkiewicz, M. Damayanthi, Y. Danca, D.M. Dang, H . 4 . Daniel, T. Dantale, S.W. Darses, S. Das, A.R.
IkiJa
Das, B.C. Das. N.B.
LwdL
Das, T.K. Datta Gupta, A. Dau, M.E.T.H. Davey, P.N. David, D.M. David, K. Davies, D.T. Davies, J.E. Davies, R.V. Davis, K.J. Day, M.W. De Angelis, F. De Boos, G.A. De Lombart, S. De Lucchi, 0. de Avila, E. de la Cruz, P.
i!fAamL
DAccolti, L. D'Achille, R. DAloisio, R. DAnnibale, A.
v Dahiya, R. Dai, G.-y.
IuJi%G Dai, L. Dai, L.-X.
Dainty, R.F. Dake, G.R. Dakin. L.A.
209,270 026 010 281 289 323 045, 046, 048, 119,202,232 298 029 206 123, 126, 134, 256,260 062, 198, 271 282 097
& Mattos. M.C.S, de Meiiere. 4, de Parrodi, C.A. de Soma Batista, C.M. de Souza Melo, S.C. de Souza, R.F. de Vos, M.J. De, A. De, M. Dane, P.O. DeBoos, G.A. Dechoux, L. Deel'Innocenti. A. Dehmlow. E.V. Deka, N. JkKimpe. N. Delgado, M.
164 134 105 153, 188 163 243 011, 149 098,099, 224 185 080 166 03 1, 203,266 110 008 044, 097, 152 311 041 307 135 27 1 104 091,093,337 109 120 044
108; 284 234 230 038 301 139 336 037 312 093,097 018 048 048 078 038 199 321 298 230 219 263,320 182 143 074 226
356
DeMario, D.R.
I%bakA&
DeMico, A. Bmir. A.S, Jkmonceau. A DeMoute, J.-P. Deng, L.X.
llamwLw deNooy, A.E.J. DePascali, F.
-
l2ablUL Mrien, S.
I2G?3xA
Derrien, N. Desai. D.G. DeschEnes, D. Deshpande, A.B . Detomaso, A.
l2aLmL
Devasagayara, A. Devasthale, P.V. DeVos, D.
QGYQLRL
Dgirmenwi, N. Dhuru, S.P.
Diaz-Domhguez, J. Dickinson, M.G. Didelot, M. Didiuk, M.T. Diefenbach, A. Dieter, J.W. Diez-Bana, E. Dikshit, D.K. DiMichele, L.M. Ding, H.
RiuL
Dingess, E.A. Dinoi, A. Dishington, A.P.
lAJu4LL
pixneuf. P.H,
Compendium of Organic Synthetic Methods,Vol 10
238 125 047 201 095 099,098 155 071 164, 166,267, 264 050 321 200 322 109 018 013 0%
061 056, 1 4 7 m 007 209 2 19 089 342 169 204 049 195 077 307 029 012 083, 288 016 112 105, 112, 281, 284, 287, 325 336 314 240 016
090
087, 329 223 209,270 348 324 224, 279, 299, 322
Authors
Durant, G.J. Durr, R. Dutta, M.P. Dutta, P. Dutta, S.
341 337 038 124, 320 179 022 246 193 239 273 113 048 146 023,073 289 23 1 275 126,219 218 015 058, 309 299 230 075, 121 162095,099 055 258 129, 130 099,293 096,107 246 267 149 108,284 283 303 028, 051, 150 053, 303 078 300 069 125 301 290 055, 067, 148 251
East, M.B. gaton. B.E,
130 057
Dizi&re,R. Doan, B.D. Doas, P.I. Dobbs, A.P. Doi, M. Doi, T. Dolbier Jr., W.R. Dolhem, E. Dollinger, L.M. Domae, T. Dominguez, E.
RQxdLuL
Donde, Y. Dong, T.-W. Dong, Y. Donnoli, M.I. Donohoe. T.L Doris, E. lbE&mdu
Dosa, P.I. Doty, M.J. Doucet, H. Dove, M.F.A. Dowdy, E.D. Doye, S.
l h Y u Y E
D o z ~M.-J. , Drager, G. Driver, M.S. Drysdale, M.J. Du, H. Duan, J.
QuhLL
DuBay, W.J. DuBois, J. Dudding, T.
Dumas..
Dufiach, E. Duncan, M.P. Dupont, J. Dupuis, C.
Author Index
-
EamJL Ebitani, K.
Fkkert, M.
l2dxwML Eilbm&J!. Eilers, F. Einhorn. C. Finhorn. J. Eisenstadt, A. Eklund,L. El Ali, B. El Zaizi, A. Elizarov, A. Ellis, W.W. Elomari, s. Emami, R. End, N.
JAvklsa
rn
Endo, M.
Enholm. E.J. Epa, W.R. Epifano, F. Eshghi, IT.
EYanLRA Evans, P.
EYad2.A
Evans, T.T. Everaere, K. Ewing, G.J. Ezaka, T.
Fache, F. Fagnoni, M. Faile, J.M.
FakLuL Fallah, A. Fan. D.
236 165 064
244 344 123 136 028 049, 189 049,189 130 053 144 209 181 183 021 315 028
212 165 138, 301, 315, 316 247 252 104 197 333 041, 199, 205, 237 265 158, 209, 267 347 275 303, 311,322 243 257 204 100
127 330 232 089 278 283
Fan, R. Fang, J. Fane. J.-M, Fanwick, P.E. Farrell, R.P. Fatemi, P. Fatland, A.W. Feeder, N. Felix, D. Fell, R.T. Fenrr. J.-C, Feng, S . 4 . Femandez, E. Femhdez, I. Femhdez, K.M. Femhdez-ACebes, A. Ferraris, D. Ferraz. H.M.C. Ferreri, C . Fem, F. Fems, L. Feutren, S. Fiandanese,v. Fiedler, c. Fieldhouse, R.
Finkelstein, M. Finlay, J. Fiorani, T. Fioravanti, s. Fiorentino, M. F i O U z a U
Fischer, R. Fitzpatrick, K. Flack, S.S. Flego, M. Fleitz, F.J. Fleming. I, Fl6rez, J. Fokin, A.A. Fonck, G. Fonenas, C. Forbes, D.C. Ford, J.G. Formentin, P.
357
323 330 253 226 065,066 295 057 109 115 270 206 126 089 132 204 016 092 283 009,010 149 239 099,293 233 305 339 094 174 316 027 122 110 233,331 216 010 133,285 209 037, 141, 3I26 339 018 145 316 161 298 092, 125 174 074 329 099 159 204
358
&xtL
Fortunak, J.M. Foubelo, F.
J3.xuwA
Fragale, G. Fraile, J.M. Francesch, C. Francke, G. Frauenkron, M.
mi!cL
Frohn, M.
Jb2Ym-E l2amLuL Fu, C.-G.
F!JsG Fu, P.P.
l&hLPL
Fugami, K. Fujibayashi, T. Fujieda, H. Fujihara, H. Fujii, A. Fujii, K. Fujii, M. Fujimoto, K. Fuitmura. 0, Fujinami, M. m i s a w a T, Fujita, A. Fujita, M. Fujita, T. Fujita, Y. Fujiwara, N. Fujiwara, T.
Fujiwra, R. Fukuda, T. Fukuhara, T. Fukui, Y. Fukuma, T. Fukumoto, K. Fukumoto, Y. Fukuoka, S. Fukushima, M.
-
Compendium of Organic Synthetic Methods, Vol 10
1233 244 029, 308 067,075 019 096 174 155 093 053 164,166 110 281 055, 146 015, 038,040, 138, 179, 182, 248,255,265 243 120 005,241 075 038 109 150 035 222 049 027 215 024 093, 196, 292 081 328 221,250 081 212 092, 175, 219, 222, 227, 319, 338, 339 002, 008, 298, 305 022 093 175, 323 152 023, 273 186 307 261 222
Fukuyama, Y. F u k u z u Fukuzawa. Fukuzawa. S.-i, Fukuzumi, S. Funabiki, K. Funato, M. Funatsu, M. Fung, W.-H. Furrow, M.E. Fiirstner. A.
l2mmsJL
Furukawa, H.
FllrukawaI.
Furukawa N. Furuta, Y. Furuya, H. Fusco, C.
Gabbi, C. Gabriele, B . Gacon, A. Gaddoni, L. Gaggero, N.
GagnLXR
Gai, Y. Gajare, A.S. Gajda, T. Galardon, E. Galarza, R. Galili, N. Gallagher, D.J.
i3subdL
Galland, J.-C Gallenti, P. Gambaro, M. sauer. 4. Gao, Y. Garber, L.T.
Garcia, C.F. Garcia, B . Garcia, C.L. Garcia, G.V.
Authors
184,336 219 209 154 014,254 081 133, 134 063 323 046 248 001, 026, 065, 224,226, 227 154,252 345 034 054 298 209 209,270
342 321 209 273 236 148 070,097 147,204 120 094,291 110 094 107 255 275 101 010 248,250, 251 100, 118, 301 303 172 095 011,082, 106 011, 106 187
359
Author Index
Garcia, J.I. Gargano, M. Garrett, C.E. G m e r , P. Gasparini, V. Gauthier Jr., D.R. Gauthier, J. Gautier, A. Gautier, E.C.L. Gautier, I. Gebauer, M.G. Gelas-Mialhe, Y. Gelbard, G. Gelo-Pujic, M. GenCt. J.-PA Genov, D.G. Genov,M. , George, M.V. George, R. Gerard, J. Geremia, J.M. Gerlach, A. Gero, S.D. Gesenberg, K.D. Gevorevan. V, Ghaffarzadeh, M. Ghelfi, F. Ghosh, A.C. Gbosh, K. Ghosh, U.
Giacomini.* GiardinA, A. Gibbs, A.R. Giese, S.
Giles, P.R. Gill, A. Gill, G.B. Gille, B. Giovannini, R. Giroux, A. Gladstone, P.L. Glaze, W.
Godard, A. Godjoian, G.
GxkA
096, 232 081 040, 265 129,320 305 019 332 046
205 342 079 277 048 153 035, 098, 099, 224, 275, 300, 342 223 016 110 298 338 311 249 028 005 057, 059, 336, 339 2288 342 115 136, 203, 337 194 298 101 347 031 195 223, 318 046,047, 133 051 191 247 070, 347 126 310 165 214 135 050 238
l3QLQJL
Gogia, A. Goldring, W.P.D. Gomez-Bengoa, E. Gong, J. Gonz5lez-NuRez, M.E. Gore, J. Goto, C. Goto, S. Gottardo, C. Gottlich, R. Gouda, K. Gouda, K.-i. Gouvemeur, V. Goyal, R. Gozzi, C. Gozzo, A. Grabowski, E.J.J. Graf, R. Graham, A.E. Gramain, J . 4 . Grandi. R. Gratzl, J.S.
i.A&&LS
Greiner, A. Griffin, S.
GrkLR
Groaning, M.D. Gross, E.K.M. Grozinger, K.
cbm&mL
Gu, H. Guadarrama M, F.O. Guagnano, V. Gucbhait, S.K. Guerra-Weltzien, L. Guib6-Jamoel. E, Guijarro, A. Guijarro, D. Guillou, 0. Gunarame, H.Q.N. Gunawardena, G.U. Gundogan, B. Gunzner, J.L. Guo, C. Guo, H. Guo, Y.P. Gupta, A. Gupta, V.
102 2344 224 083 241 152 139,271 317 240,241 042 154 069 112 170 140 066 102 007,084 079 205 277 342 049 017, 019, 022 27 1 115 149 133 108, 286, 346 342 255 104 227,337 045 054
064
220 284 1533 112 034 260 233, 331 327 046,253 129,320 015,017 197
046
090, 143 104
360
Gupton, J.T. Giirtler, S. Guzzi, U. Gyenes, F. Gyoten, M.
Compendium of Organic Synthetic Methods, Vol 10
010 088 098 119 062
Hara, R.
BaGLSA
Harada, H. Harada, K. Hamcia, M.
l&uadLL
Harayama, H. Harihmsubrahmanian, H. Ha, H.-J. Haberman, J.X. Hachiya, I.
J3%uxLE
Haderlein,G. Hadida, s. Hageman, D.L. Hagiwara, E. Hagiwm, S. Haigh, D. Hair, M. Hajare, C.T. m u r . A.R, Hakiki, A.
IiaukuL
Hamachi, K. Hamada, T.
HamadaY.
Hamann, B.C. Hamann-Gaudinet, B . Hamasuna, Y. Hamelin. J,
lbawLE
Hammerschmidt, S. Han, B.-H. Han, X. Han, Y. Hanafi, N. Hanamoto, T. Hanessian. S, Hansen. K.C. Hansen, M.C.
€Ianmdx Hanson, M.V.
Hanusch-Kompa, C. Hanyu, A. Hanzawa Y. Hao, Q.-S. Hao, W. Haque, A. Hara, 0.
250, 292 020 271
094
016 032 140 069, 112 075 099,293 250 044
200,201 192 060,079, 161 027,033 027 283 129, 196 023 198 055, 200 131 016 176 309, 317 079,086 114 042, 322 342 010 160 174, 175 194 280 047 193, 274 126 327 090 283
I&xmm?x Harms, K. Harpel, S. H ~ DD.N. . Harris, C.R. Harris, M.C.
Hamwadx
IiaruLL
Hartmann-Schreier, J.
HasegawaE.
Hashem, Md.A. Hashemi. M.M. Hashiguchi, S. Hashimoto, I. Hashimoto, S. Hashimoto, T. Hasiguichi, S . Hassan, J. Hassinger, H.L. Hasvold, L.A. Hata, E.
Iiamihx HatahL
Hatanaka, Y. Hatano, B. Hatlevik, 0. Hattori, K. Hattori, T. Hauck, B.J. Hauck, S.I. Hayakawa, S. Hayashi, H. Hayashi, N. Hayashi, R. Haynie, B.C. Hays, D.S.
Authors
069,070, 340 175,323 268 301 141 022 279 172 315 317 174, 313 180 085 123 062,271 343 244 129, 130, 162 196 195 304 329 035 123 165 168 032, 180, 256 330 074 066 112 287 290 306 069,112 340 290 171 034 103 080 287 346 311 264 269 024,085, 286 243 138, 179, 182
36 1
Author Index
Hayter, B.R. He, Y.
JicxkxA
Heath, L. Heck, M.-P. Hecker, P. Hegbom, I. Hellgardt, K.
Hemming, K. &ndn 'ckson. J,B, Henniges, H. Henningar, K.A. Henry, J .X. Herb, T. Heres, H. HBrion, H. Hermes, M.
Hiaubdx
Heron, N.M. Herr, R.J. Henmann, W.A. Herzog, K.J.
lkYedL
&vdari. A, Hibbs, D.E. Hicks, F.A. Hicks, R.
HiaJL
Hideura, D.
Higa, S. Higama, T. Higashimae, Y. Hightower, T.R. Hilberath, L.A. Hildebrand, J.P. Hilliard, M. Himabindu, K. Hinzen, B. Hioki, H. Hioki, K. Hirabayashi, K. Hiraga, Y. Hirai, A. Hirama, M. Hirano, K.
248,255, 258 165 317 133 133 207 301 343 076 035,036, 310 279 218 114 086 035 214 018 239 077 313,340 083, 288 311 129 348 338 295, 343 316 153, 333, 334 164 061
212 146, 223 288 305 081 152 157,287 146 099 051 142 046 219 274, 317 069,339,340 319 240 081,088 254 037, 142, 172, 174. 204. 233.
Hirano, T. Hiranma, S. Hirao. T, Hirashita, T. Hirosawa, C. Hirota, T.
LIivano. M, €ibamJa
Ho, D. S. X . Ho, P.S. Ho, P.-S. Hodder, A.S.
Hofmann, J. Hoge, G.S. Hojo, M. Holingworth, G.J. Holla, E.W. Holliday, P.
JdQhsAL Homsi, F.
-
Honda, K.
Honda.T.
HQnLLc Hong, J. Hong, J.E. Hong, J.-B. Hong, J.-H. Hong, R.-K. Hong, S.H.
HQwla
Honma, T. Hooper, M.W. Hori, K. Hori, M. Horikawa, Y. Horiuchi, T. Horn, E. Homer, J.H. Horsburgh, C.E.R.
235,324 053 012 120, 179, 181 193, 242, 248 290 096,266 120 203 228 002,053,063 069, 112,219 220, 238, 339 340 272 099 003, 025,098 156,201, 241 224 031,032, 192 214 223, 318 166, 268, 323 080 244 028
109 304 279 030 250 270,332 108,284 197 187, 198 332 025,098, 126 332 016,017 215 132 294 294,297 092,338 266,325 053 164 054 105 239
362
Compendium of Organic Synthetic Methods, Vol10
Hosokawa, H. Hosomi. Hossain. M . G
kblLLuU HOU.
x.-L
Hou, Y. Houille, 0. Houllemare, D. Homer, J.H. Hovevda &&, Howell. A.R, Hrubv. V.L Hu,Q.-S. Hu, T. Hu, Y. Hu, Y.-H. Hu, Y . 4 . Huang, J. Huang, J.-W. Huang, M.-Y. Huang, P. Huang, T. Huang, W.-S.
iiuaux
Huang, Y. kQ. Y.-z, Huber, F.A.M. Hudack Jr., R.A. Hufton, R. Hug, R. Hughes, A D . Hujiwara, K. Hulst, R. Hume, W.E. Humpf, H.-U. Hungerhoff, B. Huo, S. Hursthouse, M.B. Husfeld, C.O. Hussain, K.A. Hussein, M A . Hussoin, Md.S . Huwe, C.M. Hwang, B.K. Hwang, J.P. Hyma, R.S.
266 069, 081, 166, 268, 323 0% 051, 121 123 126, 134, 256, 260 101 043 024 337 083, 288 239, 323 086 014 338 007 216 126
054
I93 169 293 344 014 065, 105, 107, 112, 151, 340 135, 136, 137 079, 329 261 2600 124, 125 286 103 264 018 095 244 195 339 3 16 224 225 109 218 108 022 314 277
Ibrabim-Ouali, M Ichikawa, S. Ichiyanagi, T. Ido, T. Idoux, J.P. I e h i n i , A. Igarashi, T. Iida, A. Iida, T. Ikariya, T. Ikeda,A.
JkLkLu
Ikeda,T. Ikegashi, K. Ikeno, T. Ikonnikov, N.S. Imada,y. Imagawa, K. Imai, E.
ImaiJL
Imanzadeh, G.H. Imma, H. Inaki, K. Inamoto, N. Inamoto, S.
InanapaJ.
Inesi, A. Inglis, G.G.A. Inoeu, R. Inoue, H. Inoue, K. Inoue, M. Inoue, R. Inoue, S. Inoue, T. Inoue, Y.
,J-J
la-dsL IEumas
Irie, R. Isaac, M.B. Isayan, K.
Authors
038 061 063 093, 196 103 010 098 113 109 262 035 266 158, 186, 282, 309 058
096
002, 238, 339 328 316 288 290 150 092 115 273
I50
224 299 042 110, 143 145 070 312 013,023 066 030, 076, 220 030 179 024 294, 343 166,234 071, 141, 160, 161, 260, 263, 266,326 027,033 020 293
Author Index
k?&i&
Ishiba, A.
Ishida, A. Ishida, T. Ishifune, M. Ishiguro, H. Ishihara, K. Ishii, K. Ishii, T. khii. Y, Ishikawa, T.
miULY.
Ishitani, H. Ishiyama, T. Ishizuka, T. Ishi-i, K. Itami, K. Ito. H. Ito, K. Ito, M. Ito, s. Ito, T. luLy.
u
Itoh, K. Itoh, S. Itoh, T. Itoi, Y. Ivanova, v. Iwahara, T. Iwai, J. Iwama, H. Iwamoto, H. Iwamoto. M, Iwamoto, s. Iwamura, N. Iwasa, K. Iwasaki, F. Iwasaki, N. w w a . N, Iwase, K. Iwaya, M. Iyanar, K.
Ivenear.D.S.
IYefA
Izumi. J.
265 017 282 306 345 295 150 047,101 167 224 047, 119, 143, 144, 171, 189, 257, 300 242 214 296, 300, 301 259 081 175, 323 318, 331 069, 081, 090, 268, 274, 323, 323 018, 095, 161 253,283 091 233 120, 330, 331 101, 229 029,261 233 178 053 016 189 022, 297 302 165 204,328 189 282 017 041,209 222 328 345 290 163, 231 030 077, 202 140
363
Jacobs, P.A.
Jacqualt, P. Jacquesy, J X . Jacquier, Y. Jaeschke, G. Jagodzirlski, T.S. Jakhi, M. James, R.A. Jamison, J.A. Jana, U.
Jiuliaa Jang, S.-B.
Jang, W.P. Janssen, J. Janssen, J.P. Jare, S.S. Jkzay, Z.M. Jayasree, J. Jeffery, T. Jeon, D.J. Jeon, S.-J. Jeong, J.U. Ji, J. Jia, Y. Jiang, Q. Jiang, W. Jiang, Y. Jiang, Y.-Y.
-
Jim, X. Jim, Q.-H. Jim. T-S. Jin, B.W. Jin, J.
linM&
Jin, Q.-H. Jin, T.-S. Jin, W.-S. Jin, Y.Z. Jnaneshwara, G.K.
265 287 204 097, 248,284 317 055 033 132 087 280 116 102, 141 328 051, 194 178, 179, 214 227 003, 078,099 194 197 036 310201 100 152 099 261 091 114 088 023 034,035 005 034,035 169 126 001 020 055 167 074 017 024, 180
040
298 322 204
364
JdlammA
Johansson, F. Johnson, E.S. Johnson, J.S. Johnson, N.B. Jon, S.Y. Jonas, L. Jonasson, C. Jones, A.D. Jones, D.E. h E L L
Jones, P.G. Jones, R.V.H. Jones, T.K. Joo, Y .H.
JihmauA
Joshi. G.C. Joshi. N.N. Jouannetaud, M.-P, Joung, M.J. U m a u x . Y,
JiuKLkL
Juang, B. M s t i . E, Julia. M. Julienne, K.
JiuaiL
Jung, A. Jung, D.-S. Jung, L. Jung, W.-H. Jurka, J.
JJmluL Juteau, H.
Kablaoui, N.M. Kache, R.
JGLGL
Kademit, D. Kadota, I.
Compendium of Organic Synthetic Methods, Vol 10
131 122 226 347 073 150, 151, 191 171 326 283 315 124
079 094, 159 123 214, 227 128, 136 232 018 033 240 204 240 010
018 070,097 160 187, 198 206 258, 304 188 286 015, 018 255 009 090,096
025, 129,175, 222, 243, 244, 250, 268, 269, 326, 332 153, 333 043 050, 170, 171, 311 167 059
Kagawa, M. Kagoshima, H. Kahl, S. Kai, H. Kainz, S. Kaizer, J. Kajita, S. Kakiuchi, F. Kakiya, H. Kakusawa, N. Kalita, D.J. KiibMdL
Kamal.. Kamal, M.
Kamaol. 4. Kambara, T. Kambe. N.
Kameda, M. Kamekawa, H. Kamijo, S. Kamikawa, T. Kanai, G. Kanamori, M. Kanda, T.
KanedaK.
Kaneko, T. Kanemoto, K. Kang, C.-J.
Kanc. H.-Y.
Kang, J.-B. Kang, K.-H. Kang, S.B. Kang, S.K.
Kano, D. Kantam, M.L. Kanyonyo, M.R. Kanzler, S. Kapur, N. Karchaudhuri, N. Karimian, A. Karjalainen, J.K.
Authors
023,046 235, 269 277 180 078 110, 113 309 202 063 336 030,220 039 055 244 101, 133, 134 135,206 140 200 109 001,076, 111 306, 309 167 009, 246, 070 346 226 -
068
217 266 100 049, 155, 165 022, 139 163 163 247 210 080 292 249 127 001, 003, 025, 060, 061, 078, 098, 099, 126, 156, 194, 201, 241, 319, 338 114 313 102 343 104 199 343 164
365
Author Index
-
Karlstrom, A.S.E. Kamik, M.A. Karodia, N. Kasahafa, y. Kasatkin, A. Kashima, M. Kashinatham, A. Kashiwagi, y. Katdare, S.P. Kato, A. Kato, H. Kato, K. Kato, M.
KiLGL
l.GU22
Katoh, M. tzkv. A.RL
?sawLI
Katsuyama, 1. Kaur, G. Kaur,H. Kaur, J. Kaur, K.P. Kawaguchi, Y. K a w a h a , R. ~awahafa,M. ~ a w a h a r N. a Kawai, M. Kawai, s. Kawaji, T. ~awamoto,K. Kawamura, T. Kawamura y. Kawaragi, S. Kawasaki, I. Kawasaki, K. Kawasaki, T. Kawasaki, Y. gawashima. T, Kawatsura, M. Kayano, A.
a K m m i , F. Keav.B.k KakaL
074 232 239 167 095,243 172 191,295 080 145 022, 039, 072, 191 137 274 014 286 276 100 141 250 052,294,297 018, 027, 033, 093, 095, 113, 115, 161, 235, 262 133, 134 025,054,317 317 140,171 170,311 033 181 184 311 266 315 123 183 063 101 063 255 113 254 143, 144, 300 224 068 345 298, 155 160,161,266 043 283
J.W. Keith, J. Keller, E. Kellogg, R.M. Kells, K.W. Kenney, P. Kent, J.L. Keppens, M. Kercher, T. Kerekes, A D . Keshavaraja, A. Kesten,S. K e n , G.
-
Khanapure, S.P. Khanna, V. Kharamesh, B . Khare,A. Khasnobis, s.
Kianfar, G. Kiba, T. m a s h i . c. Kicla, M. Kiehl, 0.c. Kiesman, W.F. Kiessling, A.J.
IOYLL
Kiji, S. Kikuchi, D. Kim, B.H. Kim, B.S. Kim, B.-K. Kim, D.I.
s
Kim, D.-Y. . Kim,H. Kim, H.-S. Kim, I.K. Kim, J.
Kun.J.N. KimsL
Kim, J.Y. Kim, J.-H. Kim, J.-K. Kim, J.-S. Kim, K.M.
KblLL
105,107 080 089 018 086 017 005,223 074 300 005 011,149 102 249 049 201 205 234 055 049 201 169,203,221 234 200 051 015 241 108 073 146 022, 152, 197 325 171 135 314 176 135 102,345,346 347 025 096 091 102 179 097 022,098 145 052 311 338 141,261 150, 151,191
366
Compendium of Organic Synthetic Methods, Vol10
u Kim, S.-H. Kim, T.H. Kim, T.-H. -
Kim, W.-Y.
KlmJ
Kim, Y.-M. Kimachi. T, Kimura, A. Kimura, K. Kimura, M. Kin, J . 4 . Kinoshita, A. Kinoshita, A. Kira. M. Kirihara, M. Kirova, M. Kirschberg, T.
Kise, N. Kishida, M. Kishikawa, K. Kiss, T.
KitaJL KihL
Kitahara, N. Kitahara, T. Kitajima, H. K i m u r a , M. Kitamura, T. Kitazume, T. Kizito, S.A. Klaubert, D.H. Kleiner, K. Klement, I. Kling, R. Klucik, J. Knight, F.I. Knobelsdorf, J. Knochel. P,
213, 334 127 192, 194,248 347 078, 098, 099, 194 091 001, 156,241 249 080, 091, 115, 117, 167, 314, 348 247 254 275 267 240, 279 126 212 297 016 308, 325 333 330 258, 304
064
025 306 086 232 062 038
008
018,095 089 002, 298, 305 195 254
Knolkner. H.-J, Knowles, H. KO, S.-L. Kobata, M. Kobayashi, K.
Kobayashi, T. Kobayashi, Y. h b a v s h i . S, Koch, D. Kochi, J.K. Koda, G.
xsQdaU& Koga, G.
IwiLKa Koga, Y.
Kiluix
Koh, K.S.-V. Kohmoto, S. Kohmura, Y. Koike, N. Koike, T. Koizumi, T. Kojima, A. Kojima, R. Kokubo, C. Kokubo, K. Kolomitsyn, I.V. Kolter, D. Komatsu, M.
199
324 147 024, 039, 168, 193 309 010 283 132 102 016, 024, 038, 039, 068, 076,
Komatsu. N. Komiya, K. Komura, K. Kondakov, D.Y. Kondo, K. Kondo, S. Kondo, T.
JCQu&LL Kong, M.S. Kong, N.
Authors
088,089, 168 193, 198 079 106 336 222 095,298 024, 102, 105 122, 148, 189 247,267, 269 270, 271, 291. 295, 296, 299. 300,301 329 265 27 1 227. 309 235; 346 228 219 304
044
105, 148 319,329 210 268 306 113 141 150 , 335 227 132,209, 299 235 331 174 287 032, 111, 114, 142, 150, 151, 180, 306,309 056,234 228 188 070 040,079 109 103 125, 332 024,255 346,347 093
--
367
Author Index
--
Kong, S. Konishi, H. Konishi, K. Koniya, N. Konno, K. Kono, K. Koo, J.S. Koo, s. Kopecky, D.J. Kordes, M.
IQmda= Koseki,Y .
Kotora, M.
M
Kou, y. Kouge, K. Kowase, N. Kokvar, M. KoSmrlj, J. Kraft, A. Kramps, L.
KwiLE
M
Kreimman, S. Kreutzer, K.A.
KsfA
Krishnamurthy, v Kroutil, W. Kubato, C. Kubo, T. Kubota, H. Kubota, K. Kubota, y. K u b o y m , J. Kudo, H. Kudo, K. Kudoh, H. Kuhling, K. Kuhnau, D. Kuhnert, N. Kulasegafm, s. Kulawiec. R.J. Kulicke, K.J. Kulkami. M.G. Kulkami, S.A. Kumagd, N. Kumar, B. Kumar. B.A.
208,317 298 113 190 033 274 208 135 027 231 093 149 285 075 004,070,341 066,086, 116, 117,266 142 092 274 325 325 182 315 148 004,269 111 050 038 1% 316 016' 181 208 078 150 323 235 032
Kumar, D.
Kumar, J.S.D. Kumar, K. Kumar, M.S.
-
Kumaf, V.V. Kumarm, G . Kumafeswaran. R. Kumbhar, P.S. Kume, K. Kunath, A. Kunishige, H.
Kuniyama, s. Kurashima, F. Kurihara, H. Kurihara, M. Kurihra, T.
-
JLwaL
Kuro, H. Kuroda y. Kuroki, T. Kuroki, y.
Kurusu, Y. Kusama, H. Kusano, s. Kushino, y.
Kutsuna, T. Kuwmo, R. Kwon, 0.0. Kwon, P.-s. Kwon, S.Y.
124 140 157,210,246 110 232 045,210 169,259 295 347 143 316 292 147 003, 242,321 180 274,317 196 145 047 167 148 039 090 181 279 265 238 025,277 319 285 144,309 063 155 180 120 013 247,311 013 247,311
009
016 128 084 192 052,192 019 320 055 016 140 052
La, B. Labande, A. Labo, A.M. Lachgar, M.
244 297 292 192
368
LadlWAR Lahoz, L.
u
Lakhrissi, M. L a k m i i y a n a , B. Lakouraj, M.M. Lakshminarayana, V. Lamarque, L. Lambert, D.M. Landino, L.M. Lando, V.R. Landre,P.D. Laneman, S.A. Lang, H.
Lanea.F.
Lange, U.E.W. Langemann, K. Langer, F. Langer, T. Langkopf, E. Lapeva, T. Laporerie, A. Lardicci, L. Larhed,M. Larock. R.6 Larsen, R.D. Larter, M.L. Lasterra-shchez, M. Lattanzi, A. Lauentsein, 0. Laurent, S. Laurent-Robert, H. b t e n s . M, Laux, M. Lavenot, L. Lawrence. N.L Laxman,E. Laxman, N. Laxmi, Y.R.S. L h o , B. Lazarus. M. Lazny, R. Lazzari, D. Le Boisselier, V. Le Maux, P. Leach, D.R. IdlYJJX Lebel, H.
Compendium of Organic Synthetic Methods, Vol 10
048
082 146 218 134 031 I38 302 102 334 305 340 130 294 336 134 226,227 088 035,036 224 225 267 045,064, 220 060,079, 161 058, 065, 121, 157, 185, 226, 297, 309, 317, 287 240 017 316 186 174 100 267 262, 322 269 066
203, 214 101, 135 101 030 232 244 138 125 028 291 231 310 090.096
LeBoisselier, V. Lebreton, J. Ledford,B.E. Lee. A.S.-Y. Lee, C.P. Lee, c.-s.
LefLui
Lee, D.-Y. Lw, G.-P. Lee, H. Lee, H.J. Lee, H.-W. Lee, I.S. Lee, J. Lee, J.A.
l&U!G
Lee, J.E.
I&Lw Lee, J.I. Lee, J.R. Lee, J.-W. Lee, K. Lee, K.C. Lee, K.-S.
LSJLJi
Lee, N.Y.
LQLlx
u
Lee, S. Lee, S.S. Lee, s.-g.
LixLxJL
Lee, Y.S. Lee, Y.-T. Lee-Ruff, E. Legido, M. Legrand, 0. m t o n . JT., keitner. W, Lekhok, K.C. LeLagadec, R. Lemaiare-Audoire, LeMaux, P. Lemoine, C.A. Lenges, C.P. Lenz, R.
s.
Authors
150 154 216 041,056, 292 031 188 189 187 0322 198 097 003,078,099 126,194 117 043, 091, 096. 190, 195 049 140,270, 324 332 049 140,208 073 311 346 167 017 188 334 195 048 107 018 167 314 348 319 094 110 014 278 227,309 337 326 300 066,127 094 095 187 172 046,048
Author Index
Le6n, G.
!d&md&
Leong, W.W. LeRaex, C. Leroy, R. Lesieur, D. Leung, M.-k.
LeLLL Leydet, A.
Lhermitte, F.
UxLL Li, D.-P. Li, G. Li, H. Li, H.-H. Li, H.-h. Li, H.-Z. Li, J. Li, J.-T. Li, N.-S. Li, S. Li, S.J. Li, S.-H, Li. T.-S. Li, W. Li, X. Li, X.-R. Li, Y.-Q. Li, Z.-Y.
J.dLx&
Liao, P. Liebscher. L Liepold, B . Lim, H.J. Lim, K.-H. Lim, Y .-G. Lin, G.-J. Lin. G . 4 , Lin, J. kin. J.-M, Lin, M.-H. Lin, N.-S. Lin, W.-C. Lindemann, U. R.J, Lindstedt, E.-L. Linney, I.D. LiDshutz. B.H,
211
090,170
317 267 256 102 193 046,048 140 198 020, 249, 257, 261,276 126 129 137 158 193 056 007,077 056 222, 269, 332 007 105 042, 056 040, 042, 055, 146 233 167 025,268 020 264 056 137 280 003 249 201,241 080 207 264 054 158, 321 253 268 279 254 306 131 285 080,083
369
Liptak, V.P. Littler, B.J. Liu, B. Liu, B.-S. Liu, C. Liu, H.
LiuJLL
Liu, J.-M. Liu, P. Liu, Q. Liu, S.
Lo, W.C. Locatelli, C. Locati, L. Lochtman, R. Logan, S.R. Loh. T.-P.
LQluaum
Lombardo, M. Longoria, M.A. Lopez, R.M. L6pez, R. Lorenzo, E. Loreto, M.A.
-
Lou, w.-x. Louie, J.
IdQwLL
Love, J.A. Lowney, D.G. Lozeva, A.M. Lu, C.V. Lu, L. Lu, L.-H. Lu, P. Lu, S.-J. Lu, w.
LuL
Lu, Y.-Q. Luchaco, C.A. Luche, J.-L. Lukin, K. LUO.F.-T. Luong, T.K.K. Lupattelli, P. Llitjens, H. Lutz. c.
276 255 206 321 032,256 328 041,072 126 023 239 010 285, 300, 333 020 094 332 234 138 131, 132 025, 084,268 272, 291,294 252 273 095 179 192 185 133 048,049, 185 185 129 030, 113, 194 336 224 342 047 171 279 048 327 142 286 089, 167 276 083 175 236 113,336 154 233 168 016,088
370
Lutz, G.P. Luzikova, E.V.
Compendium of Organic Synthetic Methods, Vol 10
107 001
Makioka, Y. Makosza, M. Malacria. %I
bk!m&3&
Ma, J.
MaA
Ma, Y. Ma, Y .D. Ma, Y.-R. Ma, Z. Ma, Z.-H. MacCiatelli, D. Machiguchi, Y. Machrouhi, F. Mack, S.R. MacLean, B.L. Macs&i, I. Maddrell, S.J. Madhavan, S . Madhusudhan, P. Madler, M.M.
MaedaJL
Maeda, K. Maeda, M. Maekawa, H. Maeshima, T. Maggi, R.
Magrath, J. Mahanty, J.S. Mahboubghah, N. Mahesh, R. Mahler, R. Mahmood, S.J.
bJamakR Maignien, S. Maiti, G. Majee, A.
Maietlcb..
Mak, T.C.W.
mkiA
Maki, T. Makihara, I. Makihira, I.
065
001, 307 340 247 055 3 14 169 149
044
148, 269 298 086 308 316 028 080 010 185, 203 064, 218, 221 092 027 150 055, 157, 202, 299, 335 204 324, 342 321 201 244 155 051 046, 253, 259 225 186 234 043
119, 124, 185, 212 164, 330 094 033,053 041,106 039 022, 072
M a l d o ~ Q ,L.A. Malik, K.M.A. Malladi, R.R. Malvestiti, I. Mamposo, T. Mandal, P.K. Mangeney, P. Manju, K. Mann, E.E. Mann, G. Mannina, L. Mannucci, S. Manz, B. Marcadal, C.
MalSbAG
Marcotullio, M.C. M~~COU X, J.-F.
ta.R
Marinas, J.M. Marinelli, F. Matino. J.P, Markmtf. J.K Mark6 I.E, Marquais, S. Mhrquez, T. Marsais, F. Marsden, S.P, Marshall. J . 4 . Marson. C.M. Martin, A. Martin. J.D, Martin, R. Martinez, C.A. Martinez, I.
Martini, 0.
Maruyama, Y. Marzi, E. Marzi, M. Marziali, P. Masaki, Y.
Authors
002,298 199 213 045,064, 220 307 316 222 257 245 055 029,087, 290 025 149 162 308 045,220 230 189 039,204 305 041, 199, 205, 237 128, 162 047 031,040 242 088 110 046, 047, 320, 324 078 245 135 099,321 020,240 278,313 033 226 190 153 192 192 116 019, 021, 051, 228 063 299 138 346 014
371
Author Index
Iblasaki.Y.
Masamune, s. Jvlashr-
-
Massah, A.R. Mastrorilli, P.
b,ladaL Mathew, J. Matsu, K.
Matsubara, y.
MamdaL
Matsuda, H. Matsuhashi, H. Matsui, H. Matsui, M. Matsukawa, y. Matsumasa, K. Matsumoto, s. Matsumoto, y . Matsumura. y, Matsuno, T. Matsuo, J.4. Matsuo, T. Matsushima, M. Matsushita, M. Matsushita, Y.-i. Matsutani, H. Matsuura, H. Matsuya, y . Matsuzaki, H. Matt, C.
hLk3ua
W e m . R.-HA Matui, C. Mau, A.W.-H. Mavers, u. May. S.A. Mayer, D.M. Mayer, M.F. Mayer, s. Mayon, p. yavoral. J.A.
M
Mazzini, c. McAnda, A.F. McCague, R.
140 223 172 232 265 081 308 256 025,277 257, 316 111 183,215,222 027 213 021 121,261 069,340 150 133, 134 213 331 326 268,296 041,106 252 105, 148 328 304 219 198 063 021 178 016 009 330 288 2% 077 216 029 275 121 260,263 316 096,232 299 154 082 036
McClure, L.D. &icCluskev. A,
I!kmuJ=
McEachem, E.J. McGill, P. McIver, E.G. McKerrecher,D. McKillop, A. McKinley, J.D. McMorrm, D.A. M m McWilliams, J.C. Medina, I.C.R. Medson, C. Meguro, M. Meiers, M. Mello, R. Menconi, I. Menezes, P.H. Meng, X.-J. Meng, Y. Menichetti, s. M h u , A. Meshram. H.M.
bmLL MaZadQ
l&LznaL
Meyer, 0. Michaud, G. Middleton, M.L. Mihara, J. Mihara, M. Mikami. K. Miki, K. Miki, T. Milenkovic, A.
w.n
ldllkdA MllkLu
Minakata, s.
167 146,348 1400 215 262 310 012 164 022 279 095,233,331 205 266 187 215 161 174 259 226,281,298 138 152 192 091 244 249,257 064; 344 219 302 056, 108, 109 140, 184, 199 200,233 174 084 195,277 155 160 301 224 292 027 214 179, 180,326 109 089 127 263 065,066 106,227 032,111,114 150.180
372
Mingardi, A. Mino, T. Minutolo, F. Mioskowski. C ,
Mirafzal. ct& Mina, A.R.
Misun, M. Mitoma, Y. Mitra, J. Mitra, R.B. Mitsudo. T, Mitsutome, A. Mitten, J.V. Miura, K.
Miura, T. Miura, Y. Miyachi, Y. Miyafuji, A. Miyagi, Y. Miyai, T. Miyami, T. Mivara. N, Miyashita, M. Miyata, N.
Compendium of Organic Synthetic Methods, Vol10
090 203 168 009, 207, 219 047 076 170 170 082 123 078, 199 078 306 125, 332 257 029 069, 081, 268, 323 061, 144, 158, 220, 309, 331 021 140
339 262 029 013,023 060 259 021 167 021, 070, 098, 217 023,273 222,243 027,222 329 088 272 346 270 016 299 212,228 042
Miyoshi, N. Mizuno, M. Mizuno, T. Mo. X.-S, Mobley, T.A. Mochida, K. Mochizuki, T. Mock-Knoblauch, C. Mofid, M.-R. Moggi, P. -haddam. F.M, Mohamed, M. &lohammadm -Baltork. I. 055, 161, 200 Mohan, G.H. 030 Mohan, J.M. 134 171 Mohanty, P.K. 157,210 Mohapatra, S. 187
-
Molinaro, C. Molteni, V. Momeni, A.R.
lY%nwcL
Monaco, K.L. Monobe, H. Montchamp, J.-L. Monteiro. A.L. Montero. J.-I, Monteux, D. Montgomery, J. Montierth, J.M. Montieth, M.
-
MQslasL
Moore, P.R. Moracci, F.M. Morales, J. Morda, D.M. Morera, E. Morgan, P.
MQLA Mori. M.
Mori, T.
MQriL Morikawa, 0. Morimoto, J. Morimoto. T,
Morioka, K. Morioka, M. Morisaki, Y. Morita. D.K. Moriuchi-Kawakami, T. Moriwake, T. Moriwaki, M. Moro, M. Momson, J.A.
Authors
115 034,075,076 085, 121, 260 267, 276,284
090
116 171 308,325 122 172, 174 183 078,305 140 113 230 238 286 274, 331 099, 121, 137 291,293 275 110 209 085 263 111 316 002, 069, 081, 238, 339, 340 015, 026, 058, 212, 213, 287, 294, 297, 319 230,290 345 053, 303, 333 298 119 037, 142, 172, 174, 204,228, 235, 307, 324, 233 049 023 125 165 121 024 271,291 024 318
Author Index
Mortreux, A. Moscalenko, M. Mossman, C.J. Moughamir, K. Mouries, V. Movahedi, Z. Movassaghe, M. Moynihan, H.A. MozzicAiwldo, A. Mucciioli, A.B. Muchetti, C. Mudaliar, C.D. Muguruma, Y. Mukaiyama, T. Mukhopadhyay, C. Mulholland, K.R. Miiller, G.H. Miiller, P. Miiller, S. Miiller. T.E, Muiioz, E. Murahashi, S . 4 .
MllratA MluidL biuaiL Murai, Y.
Murakami, C. Muraki, T. Muralidhar, B. Muramatsu, H. Muraoka, H. Murase, H. Murata, M.
bhriuas
Murata, Y. Muromachi, A. &lumav. R.W, Murthy, P.S. Mushmaf, M. A. Musson, A. Mutoh, K.
Mllzalu MymdLG
084 257 316 116 174 005 263 177 167 3466 348 157 172, 232 248 036, 107, 140, 290 137, 188 122 334 132, 317 003, 138 118 084 188, 190 264 113, 307, 336 100 191, 295 166, 323 330, 331 109 171 045, 183 133, 134 306 191,295 308 3 12 302 144 163, 231 232 045 230 154 186 027, 177, 214, 34 1
Nadi, S. Naeimi, H. Nagahara, K.
Naeao.Y.
Nagaoka, Y. PkuukLL
Nagashima, S . Nagata, K. Nagata, T. Nagayama, S.
Nagino, C. Naicker, K.P. Naimi-Jamal, M.R. Nair, L.G.
= EkimL
Naka, H. Nakada,S.
HakammA
Nakahara, S . 4 . Nakahigashi, J.
i!Q&&x
Nakajima, A. Nakajima, K. Wiima h.z M i m a . N. Nakajima, T. Nakamura, A.
kwamw&
NakamwH. Nakamura, K. Nakamura, M. Nakamura,S. Nakamm, S.-Y. Nakamura, T. Nakamura, Y. Nakanishi, A. Nakano, H. Nakano, K. Nakao, J. Nakasbima, H. Nakata, D.
lYa!aax
373
174 264 111,151,309 222 219 285 123 178 036, 107 024, 102, 122 247,267,269 270,295,299 300 229 105,249 294 257, 316 257,316 289 054 150 184,287 034 * 175,323 015,273 335 339,341 165 207 328 175 033, 078,240 133, 134, 296, 302 296 240 166 323 304 180 233 016,017 089 076 017,268 317 012,111
374
Nakatsuka, Y. Nakayama, K. Nakazawa, M. Namv. J.-L, Nanda, B. Nandanan, E. Nandy, S.K. Nanke, T. Naota, T. Napieraj, A.
LlaaaaL
Narasimhan, K.M. Narayana, C. Narender, R. Narsaiah, A.V. Nascimento, M. de G. Naud, J. Nayak, A. NWkeC, J.-Y. N&dklec. J.Y. Nuklec, J . 4 . Negele, S. Nepishi. E, Negoro, N. NBgri, S. Neidigh, K.A. Nelson, E.C. Nelson, S.L. Nelson, T.D. Nenajdenko, V.G. Newcombe, N.J. Newman, C. Newman, L.M. Ng, R.A. Nguefack, J.-F. Nice, L.E. Niemann, T. NigaI, J.N. Niguma, T. Niimi, K. Niizuma, S. Niknam, K. Nishibayashi, Y.
Compendium of Organic Synthetic Methods, Vol 10
267 189 306 023, 046, 148, 269 031,203,266 008,252 277 120, 193 190 120 319, 329, 336, 346 051 028 025, 175, 250 052 207 145 220 031,203,266 069 170, 193 090 188 004, 040, 079, 183 221, 250 009
131 010 234 044
082, 202 275 307 036 318 002 325 132, 133, 302 129,320 182 055 032 325 213 265 035,061 184,287, 311 058. 294. 311
Nishide, K. Nishieuchi. L Nishihama, S. Nishihm. Y, Nishikori, H. Nishimura, T. Nishitani, T. Nishiuama, Y. Nishivama. T, -a.
Y.
Nitta, A. Niwa, H. Niwa, N. Nobili, F. Noda, K.
iQ.&iL NQdeLu
Noe, M.C. Noels, A.F.
UQLL
Nomura, M. Nomura, N. Nomura, N.M. Nomura, R. Nomura, T. Nongkunsam, P. Nonoyama, N.
NixrhAL
Noureldin, N.A. povori. R,
Nozaki, K, Nozaki, N. Nudelman. N.S, Nuvent. W.A.
O'Mahony, D.J.R. OMeara, G. Oare, C.A. Obata,K.
Authors
179, 180 027,214 214 002,069,070 081,238,339 340 115 047 119 257 070 144, 189,261, 300 081 053 100 204 042 172 179, 180 25 1 095 188 021,092 144, 158,220, 309,331 074 061 252 092 109 230,293 316 189 035, 074, 089, 168, 185 053,282 319 187 312
285 135 313 179, 180
Dblinger, E. W a i n , M. Qchiai. M, oda,H. odenkirk, W. Ofial, A.R.
v Ogasawara, M.
-
sw=A.
Ogawa, M. Ogawa, S. Ogawa, Y. Ogiyama, H.
Oeum.N.
Oguri, M. Oguro, D.
SUxL Oh, S.-J.
c!LL
Oh, Y.S. Oh-mi, S. Ohara, M. Ohara S. Ohashi, H. Ohe, K. Ohgo, Y. Ohira, R. Ohishi, T.
QhkdL Ohno, A. Ohno, K.
i2bsauA
Ohshima, y. Ohshiro, y. Ohta, M. Ohta, S. Ohta, T. Ohtsube, M. Ohya, S.
QLL
Oishi, A. Oishi, M. Oka, M. Okada, K.
375
Author Index
172 274,331 193 233,241 075 021 299 032, 123 085 120, 179, 181, 193, 242, 248, 290 168 133,134 026 063 029 345 229 180 197 292 293 140 098 237 101 261 035,047 180 132 116,117 343 185,203 059, 228 197,323 178 150 150 344 255 034,053 062 120, 179, 181, 193 024 117 228 2% 211
O
W N.
Okada, T. okamoto, J. okamoto, s. okamoto, Y.
-
swnQL
Okazaki, R. Oku, A. Okubo, y. Okuda, T.
Okumura,, s. Okuro, K. O k u y W , K. okuyaaa T.
Q!lua Olivero, S. Olofsson, K. olrizu,
c.
s?kmlJ slnamcL
Onishi, Y. Onoue, T. Ooi, T. oppolzer, W. orioli, P. Orita, A.
021 332 185 095 335 022, 152, 197 224 022 326 142,309 228 228 110, 144,331 255 241 1766 051 060 316 131 186
060
047 021,051 078,095 017 113,243,257 042, 320, 044 s!rumaJ 316 orizu, c. 341 QciuiL 111 QmLG 209 145 QdL 111 Osako, K. 030,064,070, 075,076, 091, 211, 218, 220, 221,304,304 066 Oshisi, T. osowska-Pacewicka, K. 120,130 222 Otake, T. 081, 243, 257 QmaL 236 Ottolina, G. 030 Ousaid, A. 194 Oussaid, A. 024 outurquin, F. 211 286,302 115 Oya, S. 024, 269, 291 Oyamada, H.
-
376
Ozaki, F. Ozawa, M. Ozgiin, B.
!a€LL
Pack, S.K. Padiya, K.J. Padmakumar, R.
Pae, A.N. P.C.B. Pagenkopf, B.L. Pai, S.G. Pal, M. Palano, D. Palmgren, A. Palombi, L.
m.
!2&mQ&
Palovich, M.R. Palucki, M. Pan, 0.-G. Pan, S.-F. Pan, Y. Panda, A.K.
l?imdaG
Panek. J,S, Panyella, D. Papa, F. Papa, P.
I?auadA Pardo, D.G.
Park, C. Park, H. Park, H.S. Park, Y.S. Parlanti, L. Parmar, A.
I3ucnum Pasquet, M.J. Pasta, P. Pastori, N. Pastorio, A. Patel, P.P.
IiwxaaJ
Authors
Compendium of Organic Synthetic Methods, Vol 10
229 063 049
Pathak, A.K. Patil. V.J. Pattenden. G . Paugam, J.P. Paul, C.C. Paul, V. Pavlidis, V.H. Pchelka, B.K. Pearson, N.D. Pease, J.E. Pecchi, S. Pedragosa-Moreau, S.
297 311 195 029, 037, 086, 189, 301, 347 125 210 164 014, 333 061 003, 321 147 318 186,262 110, 113 020 162, 196 292 073 137 203,234 127 023,097, 338 168 271 080 020, 309 281 199 270 074 091, 115, 117 107,245 047 140 103, 104, 106, 117 012 236
Perez G., R.M. Perez, G. S. Perez, J.A. Perez-Andn3, J.A. Periasamv. M. PQichon, J. Perio, B. Perkins, G.
335 340 289
€!€&A
054
F!&dJL Pei, J.
l!cwLuz
Penalva, V. Pendharkar, D.S. Pepper, N.C.M.W. Pereyre, M.
l%wJLLJ.
Perosa, A. Perry, M.C.
l?x€Lu Pertici, P. Pesce, A. Pesiri, D.R.
Peterson, K.P. Petit, A. Petit, P. Petnehky, I. Petragnani, N. Petri, A. Pettifer, R.M. Peverley, J. Peyrat, J.-F.
167 216 191, 197,230 090,170 067 259 024 177 153 099,293 017,019 263 252 011,082, 106. 204,221 268,272 133,285 245 066
320 018 067 054 054 054 * 125 265 247 069 055 080 258 036 169 177 252 289 165 176,216 185,287 113 175 100
091
168 070, 347 106, 117 084 174 082,165
Author Index
Phan, N. wukan, P. j % m c w Pichota, A. Picione, J. Pickering, D.A. Piquet, M.
Porter. N.A. Postel, M. Potter, G.A. Potthast, A. Poupaert, J.H. Pouranshirvani, Sh. Powell, N.A. Pozzi, G. Prabhakar, S. Prabhu, K.P. Prahlad, v.
2766 294 047 087 051 029 224,279 158 049, 189 310 165 265 095 209 034 168 242 202 198 121,137 220 183 075 277 084 342 325 053 056 147 243 104 054, 252,272 088 028, 150 036 049 102 054 004,063,239 309 292 131 183
Prakash, G.K.S. lbkisha
054,066, 084, 135, 136, 190, 200, 290, 327, 335,337 176 053, 147, 303,
Pierre, J.-L. Piers, E. . . ...
mP. Pietruszka, J.
J2huL.A
Piilero, L. Pinho, P. Pini, D. Pini, E. Pisani, E. Pistad, V. Pitts, M.R. Pivsa-Art, S. Plath, C. PlC, G. Plietker, B. Plunian, B. Pogatcbnik, D.M.
€kkiM&
Polla, M. Ponde, D. Ponde, D.E. Ponrathnam. S, Pons, J.-F.
l?Qm&
l?GmLL
Prasad, K.G. Prasad, K.R.K. Prieto, P. hokes, I. Prokopowicz, A.S. EUJ, Puniani, E. Punzi, A. Pupowicz, D. Pumikovic, B.
I3nLui Pyun, S.-J.
377
333 260,263,264 028 018 077 102, 141, 145 175 334 014 258 305 093 108 135 078,098,099 194,319
c2imx.
344 015,017 057 135 297 028 309 018
Raabe, G . Raber, J.C. Radhakrishnan, u. Rafel, S. Raffeny, P. Rag, A. Rahim, Md.A.
016,316 266 247 310 120 234 319 074 115 080 243,259 143 011, 149 137 077 247 077
Qiu, J. Quan, L.G. Qukguiner, G. Qui, M. Quiclet-Sire, B. Quignard, F. Quintero-Cortes, I>.
Rajaramam, R. Rajkumar, A.B. Raju, S.V.N. Ramacbande,r, T. Ramaswamy, A.V. Ramaswamy, V. Ramchandani, R.K. Ramesh Kumar, C. Ramesh, C.
378
Compendium of Organic Synthetic Methods, Vol10
Ramiandrasoa, P. Ramirez, A. Ramnauth, J. R a m h , D.J. Ramondency, Y. Ramprasad, D.
Ranes, E. Rani, N. J k u . B.C,
IiaLEx
Rao, G.V.
u Rao, N.V.
Rao, P.D. Rao, T.S.R.P. Rao, T.V. Rasmussen, K.G. Rasne, R.M. Rassias, G.A. Rastelli, M. Ratajczak, F. Rathmell, R.E. Rathore, R. Ratovelomanana-Vidal,V. Ravasio. N, Ravidranathan, T. Ravikumar, K.S. Ravindranathan, T.
EayaLY&
Ray, A. Ravner. C.M, Reboul, E. Reck, G. Reddy, B.S.N. Reddy, B.S.P. Reddy, B.V.S. Reddy, C.K. Reddy, Ch.K. Reddy, Ch.V. Reddy, G.D. Reddy, G.S .
076, 242 192 094 256 075 230 109 343 053, 303 032, 051, 067, 119, 124, 148, 185, 194, 212, 220
044
244 152 101, 135, 200, 206 277 232 232 136 320 164 299 049 124 346 035, 342 081 008 166, 232, 263 245 011, 056, 134, 149 1%
169 032 303 254 133,134 134 157 088 024,039,089 313 127 040, 056, 108, 109, 140, 142, 184. 199.200
Reddy, K.L Reddy, M.M. Reddy, M.R. Reddy, N.K. Reddy, N.L. Reddy, N.P. Reddy, R.S. Reddy, T.I. Reddy, T.T. Reddy, Y.R. Reed, K.W.
RaL&lL IxGwsxE
Refvik, M.D. Rege, S.D. Reginato, G. Regla, I. Reider, P.J. Reisinger, C.-P. Ren, P.-D.
Ren, Y. Renz, M. Resenfeld, A.
€3EJLL
Resta, S. Reynaers, M.
Ihel&aL
Rhee..H.
Rhee, J.U. Rhie, D.Y. Rhihil, A. Ricci. A, Rice. K.C. Richardson, P.R.
Rienneier, T.H. Ries, M. m v . J.H, Righi. G. Riguet, E. Ringgenberg, J.D. Riordan, P.D. Rische, T. Ritiani, M. Roach, S.L. Roark, J.L.
Authors
244 108, 109, 184 250 025,175 125 128 08 1 234 169 013 153, 155 077 171 121, 317 333 263 192 007,084 129 277 020, 023, 024, 073, 180 322 169 039 281 289 204 145 145 135 102 114 125 138,208 324 112, 192, 194, 248 129 304 100, 105, 333, 339 026 024,039,068 123 255 136 037 204,276 211
379
liQbmJ=
Roberts, L. Roberts, S.M.
w Robinson, P.M.
w Rdegues, O E D . Rodriguez, A.L. R&qUeZ. MA. Rogue, J.-p.
&Qkc&!d%
Rolando, c. Romea. p. Romero, M.A.
BsmJ-Q
Ronn, M. R a k e , s. Rosa, A. Rosa, N. Rosati, 0. Roschmann, K.J. Rose, D. Rosell6, A.L. Roseman, J.D. Rosenau, T.
C p -.
Ross, A.A.
w Rossi, L.
w Roth, G.J.
w Rovis, T. Rowe, B.J. Roy, R.
Rugmini, p. Ruiz, A. Ruiz, R. Rusiniak, L.
u T. Russell, Ruszkay, S.J. Rutjes, P.J.T.
153,188 191 316 084 334 135 139 067,075 289 140 205 174 190 310 145 074 322 270 326 041, 199, 202, 205,237 231 174 204 322 049 231,252 334 242 110,143 308 003 226 218,304 262 342 295 043,055 015 287 151 029, 037,086, 347 135 204 091 115 020 007 288
233,320 196 284 004,063,239 141,261,348 060 032,111,114 142, 150,151 180, 306,309
Said, B. Saidi, M.R. Saiga, A.
w S ~ IA., S&a,
A.K. Sain, B. Saini, P.K. Saini, R.K. Saito, H. Saito, K.
saito, s. Sakaguchi, S.
sakai, H. Sakai, M. Sakai, T.
s&tbaf& N. sakamoto. K.
114 209 287 147 013 137 029 123,130 244 288 114 199,231,244 270 . 283 294 026 032,180,256 002 203 232 048,233 323 076,103 059,070,081 098,217,253 336 047, 119, 143 144,171,189. 257,300 323 021, 070, 181, 217 021,149 212,297 092
380
3akmmiL Sakata, K. Sakurai, H. Salehi, P.
sakm-di
Salm6n, M. Salter, M.M. Salunkhe, A.M. Salunkhe, M.M. Salvadori, P.
scalmAL
Sambri, L. Sammakia. T. Sammond, D.M. Samritani, S. Sanchez-Valente, J. Sandanayaka, V.P.
saudhu3
Sangani, P.K. Sanghera, J.B.
sano, s. Sano, T. Sanseverino, A.M. Sanz, G. Sarangi, C. Saraswathy, V.G.
sau!kn Sarkar. A.
2?a&LuL
Sarkissian, A.
2?amadL
scaQaa Sasai, H.
sasaki.x.
Sasaki, R. sasaki, Y. Sasidharan, M.
sassman. M.B, Sato, A.
SaLL Sato, H. Sato, K.
Compendium of Organic Synthetic Methods, Vol 10
024,063,255 166 016 266 321 326 059, 336 034
m
168, 252 061 039, 204 163 163 3444 316 333 054, 066,084, 135, 136, 190, 200, 290, 327, 335,337 110
293 051 222 320 312 172 031, 203,266 051 265 067, 077, 119, 124, 148, 220 277 293 055, 143 055, 157, 202, 299, 335 154, 262, 270, 313, 314 181 175, 219 165 259, 347 182 274 095, 100, 118, 212, 301, 340 268 033, 168, 185
Sato, S. Sato, T. Sato. Y. Sato,T. Satoh, K.
SatQLL Satoh, Y. Sauv6, G. Savchenko, A.V Savignac, M. Savignac, P. Sawaguchi, M. Sawamura, M. Sawamura, N. Sawayanagi,Y. Sawyer, J.S. Scafato, P. ssXUiA Schaus, S.E. Scheirmann, V.
sak!LE
Schierle, K. Schildknegt, K. Schilling, M.B. Schlama, T. Schlingloff, G. Schlmeier, B. Schmid, P. Schmittberger, T. Schmitz, C.E. Schmoldt, P. Schmumann, H. Scholl, M.
sGhmaEl Schreier, P.
S c W e r , F. Schulte, S. Schultz, E.K.V. Schulz, H.G. Schumann. H, Schupp, 0.
sd$wuLL
Schwarz, L Scianb, G.T. Sclafani, J.A.
ScQtLu
Scremin. M.
Authors
054 328,335 058, 115,215 294,297, 319 077 308 061, 144, 148 158, 215, 220 309 014, 106 041,042 331 275,300 005, 341, 342 323 033 204 077 126 233,320 234,262 097, 248, 317 320 147 287 113,295 164 170 154 171 102 043 23 1 330 075 337 238 244 174 078 039 180 187 039 116 251 330 321 083 062 145
SmiA
Seconi, G .
m Seferin, M. Segawa, K. Seger, A. Sehgal, A. Seid, M. Seidel, G. Sekar, G . Seki, K. Sekiya, A. Sels, B.F. Selva, M.
selL=
Senboku, H. Seng, D. sensui, H. Seong, M.R. Seshita, T. Seth, S.
-
s s Shaikh, s.1.
Shakya, S.R. Shamsuddin. K.M, Shao, D. Shao, J . 4 . Sharma, M. Sharma, P. Sharma, R.P. Sharma, R.R. S h W , v. Shamless. K.B. shXL= Shekarriz, M.
w shax S b L L
Shen, 2. Sherrington, D.C. Shi, D . 4 . Shi, G . 4 .
u Shi, Q.-Z.
Shi, X.-x.
381
Author In&x
186 114 125 087 078 035 016,018 221 105 001,065 097, 152,311 154 173 204 036 204,276 009,246 277 097 069 097 070 239 188 083 202 276
045 023 221 138 264
050 326 031,203,266 284,287 147 114,166,244 334 260 168
068 216,217 268 164 298 129,320 014 046,048 205
SbLL
W L ShibahmJ”. Shibakami, M. ShibasakLM. Shibata, I. Shibuya, I. Shie, J . 4 . Shiga, H. Shiga, Y. Shigemwa, y. Shigeta, y. Shiiakata, N. Shiina, I. Shima, K. Shimanduchi, T. S h i i z u , A. Shimizu, H.
ShlmWJ
Shimizu, K. S h i i z u , M.
Shirnizu.,
S h i i z u , M. Shimokawa, H. Shimomura, M. Shin, S.H. Shin, W.S.
w Shingare, M.S. Shinokubo, H.
Shinomiya, N.
,S-
Shiozawa, M. Shiragami, T.
Shiai,M.
S h i s h i , H. Shiaishi, T. Shirakawa. E. Shiaki, H. Shiring, F. Shio. M.
137, 164, 166 168 045,307 041,072 053 173 154,227,262 270, 313,314 013,083, 119 121,261,327 133,134 117 041 058 181 034 179, 180 229 140 132,209,299 266 254 266 063,077,328 096 196,240,292 012,111,346 093 339 295 135 197 115,215,258 204 030,064,070 075,076,091 211,218,220 221,304 344 185,243,256 314,345 253 132,299 loo, 118 119,300 088 005,053,219 220 180 260 335
Compendium of Organic Synthetic Methods, Vol 10
382
Shishido, K. Shiue, J.-S. Shivaramayya, K. Shivkumar, U. Shodai, H. Shoemaker, C.M. sbQl.LL Shook, C.A. Shriver, J.A. Shull. B.I(. Shuto, S. alY!cL Sibi. M.P. Siedlecki, J .M . Sigman, M.S. Silva Jr., L.F. Silveira, C.C. Silver, M.E. Sim, K.-Y. Sim, T.B. Simandan, T. Simcox, M.T. Sinclair, D.J. Sinearam. B, Singer, R.A. Singer, R.D. Singh, A.P. Singh, C.
slnfLL Singh, Singh, Singh, Sineh.
R. S. V.
V.K.
Singh, V.S. Singhi, A.D.
simLa
Sinou, D. Sirisoma, N.S. Sivanand, P.S. Sivasanker, S. Six, C. Slawin, A.M.Z.
SmaLUL
Smith 111, W.J. Smith, H.W.
115,215 253 110 098 070 211 191,295 328 137 149 213 329 088 306 057,284 009,010 139 149 272 088, 136 282 133 094, 291 103, 348 344 050 130,258 086 306 314 050, 170, 171, 311 044 133, 169,203 170, 311 044, 097, 152, 311 314 262
SmitmL Smith, T.E. Smithies, A.J. Smitrovich, J.H. k k u s . v, Snowden, D.J.
sxudLK
sludauL Siidergren, M.J.
Soell, P.S. Sogi, M. Sohn, S.Y. Solay, M. Soll, R.M. Son, H.-J.
Song, Song, Song, Sono,
C.-S. G. Z. M. Sonoda. N,
Span, A.R. m l e r . L.A, Sparey, T.J. kamp. W.N. SDeier. G, Sperandio, D. Spero, D.M. spezzacatena, c.
002
309 127 131 008 227 133 082, 259, 328 272 126
094
Springer, D.M.
sr&uuAL
Sridhar. M, sridharan,v. Srinivas. D. Srinivas, P. Srinivasan. P.S.
Authors
233 173,230, 273 280,282, 283 299 197 027 225 125 224 005 137 114, 152 211 010 240 049 274,318 112 060,201 306 167,250 065,112, 151 167 007 260 001, 076, 111, 120, 142, 151, 179, 185, 193, 261,306, 309 280 029 062 322 288 202 337 28 1 320 342 263 028 029, 037, 086, 189, 301, 347 052 286, 346 031, 040, 142, 184, 199,200 202,203 259 244
-
383
Author Index
Srinivasan, R. Srivastava, R.S. Srivastava, S.K. Stadmiiller,H. Stafford, D.G.
aammhdE
Stammen, B. Stammler, R. Standen, M.C.H. Standen, S.P. Stang, P.J. StankoviC, S. Stanton, M.G.
slaYb%L
Stavenger, R.A. &ckhan. E. Steere, J.A. Stefani. H.4. Stefinovic, M. Stemp, G. Stengel, P.J. Stephani, R. Steven, W.C. art. J.D. Stirlinn. C.J.M. Storch, E.C. ?tlEud&
Stiidemann, T. Studer, A. Subba Rao, Y.V. Subbareddy, B.V.
Sudha, R. Sudha Y. Sudrik, S.G. Sueda, T. Suga, T.
ihk3mLK Sugawara, M. Sugawara, S. Sugi, K.D.
SUiL
Sugihara, M. Sugimoto, K. Sugimoto, Y. Suginohara, Y . Sugiomoto, Y.
046 132, 302 173 193 337 286 095 213 159 205 1% 209,267 148 325 264,267 287 215 091 225 321 284 172 233 153, 155 219 257 077 038 312 225 204 246 008, 056, 077, 134, 137, 147, 204,243,294 051 186 306 241 030 198 064,092 044
036, 107 150 215 015 322 166 042
Syamala, M. Szab6, K.J.
253 119,121 266 001 204 151 021 269 179, 193 043 164 199 296 190 069,338 229 023 231 119, 121 217 056, 103,230 234,290,293 341 195 332 296 304,305 241 002 013 291 080 209 302,308
Szvmoniak. K, SBrbye, K.
115 027
Tabaka, S. Tabanella, S. Taber. D.F. Tabuchi, N. Tabyaoui, B.
279 285 208,311 193 192 017,037 319 090, 193,274 117
Sugisaki, C.H. Sugiyama, E. Sugiyama, T. Sukbomlinova, L.I. Sukumar, R. Sumida, S.-i. Sumihara, H. Sumino, Y. Sumitbra, G. Sun, G.-R. Sun, H. Sun, P. Sun, U.J. Sun, W.-H. Sun, X. Sung, G.-F. Superchi, S. Suwa, T. Suzuki, A.
s!mLlL
Suzuki, K. Suzuki, N. Suzuki, T. Suzuki, Y. Svatoi, A. Swallow, s. Swami, S.S. Swann, E.
xlEasLL
SaaEkx
Taguchi, H.
044
384
Takabe, S. Takada, H. Takada, T. Takagi, J.
lhka&K
Takagi, Y. Takahashi, K. Takahashi, M. Takahashi. T, Takahashi, T.T.
mai&
Takaki, K. Takami, N. Takamori, M. Takanami,T. Takasuka, M. Takaya, H. Takaya, Y.
lawarMa Takeda, A.
lh4daJL
Takeda, M.
llbbk!L
Takeno, M. Takezawa, E. Takhi, M. Takimoto, M. Takizawa, S.
JaaLLaR Talukdar, S. Tamaki, K.
Tamaoka, Y . Tamarao, C. Ii3nmLL
Tamashiro, G.S.
I!AmadL
Tan, J. Tan, Z. Tanabe, K.
Tatl&Lx
Tanaka, A.
Compendium of Organic Synthetic Methods, Vol 10
172 035 062 185 026 061 203 120
139 023, 069, 070, 273, 338, 339, 340, 341 266 024, 222, 273, 344 002,008 120 227 083 275 005,053 085 033 059 335 335 008, 092, 175, 212, 219, 222, 227, 319, 338, 339, 340 144 180 047, 287 143, 187 319 232 280 178 268 031 229 013 240, 279 146 173 104 019 209,299 269 240
Tanaka, M. Tanaka, N. Tanaka, Y. Tanbaka, S. Tando, K. Tandon, M. Tang, J. Tang, M.-H.
IhQLL lh!i&
Taniguchi, T. Taniguchi, Y. Tankguchi, A. Tankguchi, Y. Tankzawa, D. Tanmatsu, M. Tanner. D. Tanturli, R. Tanyeli, C. Tao, B. Tao, S. Tapolczay, D.
2hm.a
Tarantola, F. Tararov, V. Tararov, V.I. Tardella, P.A. Tarrian, T. Tashiro, D. Tashiro, M. Tasinazzo, M. Tateiwa, J.-i. Tatsumi, T. Tatsuzawa, M. Tautermann, C. Tavlor. P.C. Taylor, P.L.
Tavlor.. l!kbcix Taybcu& Teat, S.J. Tejedor, D.
lkkdQJG
Tellado, J.J.M. Temme, 0. TemDleton, J.L, Ten, A. Temhishi, H. Terao. J.
Authors
128, 140 083,204, 306 305 057,059 042 030,075, 211 256,260 022, 039,072 236 274, 317 032, 123 002 056 008,298, 305 121 298 122 252 201 114 280 197 177 299 3 16 316 133,285 263 143 123 316 275 261 154,254 027 159,322 292 205, 275, 308, 339 029, 149 279 109 222 037 037 034 125 328 282 001.076
-
385
Author Index
Terao, K. Terao, Y. Terrier, C. Teunissen, H.T. Texier-Boullet, T. Tey, C. Thach, L.N.
lIkwM&
Thayumanavan, S. Thiebes, C. Thiruvazhi, M. Thivet, A. Thomas, R.M. Thompson, A. Thompson, D.F. Thomsen, I. Thorand, S. Thorarensen, A. Thorn, M.G. Tbornton, S.R. Tian, Q. Tillyer, R.D. Timberlake. J.W, Ting, A.Y. Tinker, A.C.
lhia&
Todd, C.J. Todd, L.J. Toduda, Y. TQULb Tohma, H.
mEJ&
Tokitoh, N.
lbkl&u
Tokunaga, Y. Tokuyama, H. Toledo, M.A. Tolstaya, T.P. Tomasini, C. Tomioka.
TQmQLL 2mLL
Tonks, L. Toratsu, C. Torchy, S. Toni, S. Torisawa, Y. Toriyama, K. Tormo, J. Tormo, J.
m
209 061 286 028 200 190
030
186 108 176 328 242 030 159 076 12%
OOQ
074 226 316 058,065 084 272 251 131 163, 305 316 149 027 171 062, 232 086, 100 224 009,246 186 184 172 001 090 109,222 175 035 076 273 126 254 184 185 182 255 315
Tosaka, E. Toste, F.D.
2lmLwL
Trananco, A.A. Tranchier, J.-P. Trehan, A.
IhhaLL
Trewhella, M.A.
lhw2laL 3mhtJAL Trotman, S.
TrouDel. ha, Truong, A. Tsarev, D.A. Tschaen, D.M. Tsuboya, N. Tsuchiya, T. Tsuda, T. Tsuge, H. Tsuji, J. Tsuji, S.
XuiiLL
l2UQdaL
Tsunoi, S. Tu, C. Tu, S.-j. Tu, Y. Tucci, F.C. Tucker. J.A. Tumas. W,
TlndQLE
Tiiter, M. Twigger, H.L.
Ubayama, H.
lJl&ahx
Ubukata, M. Uchida, M. Uchiyama, M. Uchiyama, N. Uda, M. Uda, M.
195 144 285 092 035 054
025,054, 317 082,259, 328 281,289 213 144,282 222 193 323 067 007,084 059 039, 117 144 314 181 327 063 046,047 123 101,229 142 297 298 164,166,168 088 085 165 036 316 120
338 207 330 298 024 057 056 234
386
Udodaira, K.
ueda, I.
Ueda, M. Ueda, T. Uematsu, N. Uemoto, K.
lJtmuaA Ueno, M. Ueno, S. Ueno, Y. Ufret, L.
llntL
LLkunA
Uh, K.H. Ukawa, K. Uma, G. Ymani-Ronchi. A, Umekawa, Y. Uneda, T. Uozumi. Y, Upadhya, T.T. Uphade, B.S. Uphade, T.S.S. Urabe, H. Urbano, A. Urch, C.J. Ymi. F. Usui, H. Utsunomiya, M. Uttley, M.D.
Vahle, R. Vaid, R.K. Vaino, A.R. Valacchi, M. Valot, F. Van Beek, J.
van den Hoek, D. Vanajatha, G.
m
ycimaJu
Compendium of Organic Synthetic Methods, Vol 10
346 306 021 024 035 101 035, 047,275 181 2% 165 315 209 280 043 334 204 116 017 257 298 068, 286 137, 243 077 134 212, 340 172 046,047, 108 116, 190 276 183, 215,222 022 346
287 053
Varvak, A. Vasapollo, G. Vastra, J. Vatkle, J.-M. Vaultier, M. VaZquez, E. Veal, K.T. Veenstra. SJ, VelardeOrtiz, R. Velasco, L. Velasco, M. Velu, S.E. Venkatraman, M.S. Vennall, G.P. Venturgllo. C . Verdaguer, X. Verdugo, D.
l!akLLG
Verpeaux, J.-N. Vescovi, A. Vettel, S. Vicart, N. Vicente, B .G. Vickery, B.D. Viladornat, C. Vilarrasa, J. Vinod, M.P. Visigalli, M. Visser, M.S. Vivian, R. Vocanson, F. Volante, R.P. Vrancken, E. Vyas, R. Vyvyan, J.R.
044
167 127 039 131, 132 168 237 090,143 037, 045, 046, 047, 048, 105, 119, 124, 202,
l3kdiLu
Wadgaonkar, P.P. Wagaw, S. Wagner, A. Wakabayashi, T. Wakasa, N. Wakharkar. R.D.
Authors
232, 233, 234 249 218 144,288, 307 087,087 139 084 077 124 102 112 326 192 281,325 137, 188 025,307 010 134, 160 017 058 070,097 047 016 075 322 . 002 116 190 077 147 288 127 116 080 046 161 029 114 149
023,273 044, 077, 348
128 009,207 024,269 120 077.204
Author Index
l?hkmMa Walker, M.A. Wallace, O.B. Waller. F.L
l?h!dLu
Walter, D.S. Wang, D. Wang, D.-K. Wang, D.-k.
YanaCG l 3 b L E A Wang, H.
BULL
Yang. J. -X. wang, L. Wang, M.F.
KulLLG
JmllUL
W a g , R.-P. wang, s. Wmg, T.-J.
-
wang, x . 4 wang, Y. Wang, Y.M.
XaUL
wang, z.-x. Wanninger, K. Waring, M.J. Wartuke, S.A. Waschbusch, R. Washika, C. Wasiowych, C.D. Wassermann, B.C. Watanabe, H. Watanabe, M. Watanabe, S. Watanabe, T.
l3kmakx
Watson, C. Wearing, J.T.
lm!LLL
Webb, S.A. Wedler, C. Wei, L. Wei, L.-L. Wei, X. Wei, 2.-L.
334 218 028 230 017 197 261 134 126
207 167 137, 313 054, 062, 101, 197, 301, 335 007,040 001,229,249 168 060,300 247 122 079 169 104 071 135, 136, 137 073 067,089,244 164,166,168 077 275 226
005
191 344 039 008, 058, 232 092, 209, 319, 319, 338 308,313, 314 076, 109 125 289 231 007 294 147 157 084, 291, 294 308 264
lwklL Welch, J.T.
Wender, P A Wendisch, V. Wennerberg, J. Wessie. P, W B ! Westman, G. Whelan, H.M. Whitley, P.E. Wieser, K. C.T, Wilk,B.K, Williamson, J.S.
w.
llUkd.L williamsM .J., Williams, R.M. Williamson, J.S. Wills, M.S.B. Wilson, M. Wilson, N.S. Winsel, H. Winters, M.P. Winum, Y .-Y.
EiftLL
lxQmxuu Wolf, s.
Wolfe, C.N. Wolfe, J.P.
Wolfe, M.S, Wong, J.C.Y. Wong, K.-T. Wood, S.A. woodward, S.S. Woolford, A.J.A. Woster. P M , Wright, A.S. Wright. S.W, Wu, J. Wu, J.H. Wu, J . S . w u , s. wu, w.-L. wu. Y.
387
036 224 119 224,299, 337 083 053 254 195, 327 258 120 243 273 197 342 188 266 245 293 183 036,076 216 131 163 103, 104 043 093 . 122 140 019 027 215 267 128, 129, 130 162 144 225 264,267 230 186 285 127 140 140 256,260 088 126 107 023,073 343 067
388
wu,
-
Compendium of Organic Synthetic Methods, Vol 10
z.
wu, Z.W.
Wulff-Molder, D.
YYauL
Xi, C. Xi, Z. Xia, C . 4 . Xia, J.-J. Xia, L.-J. Xia, M. Xiang, J. Xiao, D. Xiao, W.-J. Xiao, Z. Xie, B.-H. Xie, L. x u , c.
XLE
Xu, K . X .
xu, w. x u , Y.
164,166 126 254 133
338, 339, 341 338, 339, 341 142 260 256 234 005 034 307 272 142 052,294
004 084 272 327 2A6
Yamakosbi, K.
Yamamori, Y. Yamamoto, A. Yamamoto. &
Yamamoto, N.
xammaQL Yamamura, H. Yamanaka, M. Yamanashi, M. Yamaoka, M. Yamasaki, K. Yamashita. M. Yamashita, T. Yamauchi, M. Yamauchi, S. Yanada, K. Yanagisawa, A. Yanagisawa, Y. Yang, B.H.
Yachi, K.
XadaJL
Yaegashi, K. Yagi, T. Yaguchi, Y. Yakabe, s. Yamada, N. Yamada, T. Yamada, Y.M.A. Yamaguchi, K. M, Yamaguchi, T. Yamaguchi, Y. Yamaishi. Y.
218 031, 040, 043, 056, 108, 109, 140, 142, 157, 183, 184, 199, 200,210,246 345 222 141 037, 142, 174, 204, 228, 233, 235, 324 215 036, 107, 290 270 165 081,088 098, 156, 319 133, 134 209
xauJuX4
Yang, D.-H. Yang, F. Yang, H.W. Yang, J. Yang, J.W. Yang, K. Yang, L. Yang, M.
XaniLs.
Yang, S.G. Yang, z. Yanigisawa, A. Yano, T. Yao, J. Yao, Z.P. -
Yarava, J. Yasuda, K.
xasuUa
Authors
154 228 345 063 017,031,047 081, 101,229 253, 267,268 306 262 057,059,212 213,226,281 296, 298, 302 336, 339 266 184 061 179, 180 219,220 203,255 155, 184, 209 299 185 175,207 235 169 221,250 221,250 017,031, 267 145 027 243 199,200 096 145 058 250 175, 326 206 268 195 314 129,320 268 150 216, 217,291 024 020, 180 063 083 013, 023, 038,
-
389
Author Index
Yasue, K. Yatabe, K.
w Ye, J. Ye, S.
s
Yeganeh, H. Yeh, H . X . Yi, X.-H. Yie, J.
-
m Ying, T.
Yip, C.-W. Yip, J. Yokeyama, y. Yokoshima, s. Yokoyam% K.
-
Yokoyama, s. Yokoyama, y. Yoneda, E.
yonemitsu, 0. Yonezawa, S. Yoon, S.-K. yoon, Y.-Y. Yorimitsu, H. Yoshida, A. Yoshida, H.
YoshidaJ,
Yoshida, K. Yoshida, Y. Yoshihara, D. Yoshii, E. Yoshikawa, E. Yoshikawa, N. Yoshimatsu. Ma Yoshimura, N. Yoshioka, N. Yoshitake, M. Yoshizane, K. y0oda.L. Yourn, J.S. Youn, Y.S. Young, B. Young, D.J.
083, 119, 132, 209,299,327 031 042, 044 153 089 197 109 031 041 020,249,257 072,158 142 313, 327 015,016 041 109 184 222 171 308 042,212 139 175,323 181 230 074, 088, 136, 213,240 015, 156,201 213 213 030,211,304 179, 180,255 005
Yu, L. Yu, M. Yu, s. y u , w.-Y. Yuan, Y . X . Yudin, A.K. Yum, E.K. Yun, K.-Y.
xu!sx
Yusoff, M.M.
145 028 294 054 120 058,317 305 071,160 161,314
243
064
165 269 191 150 335 339 270 237 261 243 161 021,092 092 022 029 283 275
015,018 060,300 162,313 268,269, 332 046,310 126 166 121, 127,226 348 029,058,074 185.256,308 2806
Zhang..
016 015 046,048,199 200 167 268 166 016 246 333 221 137 169 139 249 015,017,034 035,073 126, 135,136 137,161, 162 197,229,249 296,301,313 314, 327, 335 169 276
390
Zhang, z. Zhang, Z.-H.
zlucddi Zhao, D.
i3wLx
Zhao, Z. Zheng, B. Zheng, G.Z. Zheng, M.
zl!wLN
Zheng, X.L. Zheng, Y.
zlNuLL
Z ~ O UA.-M. , Zhou, C. Zhou, C.-M. ZhOu, J.-Y. Zhou. L.-L. Zhou, Q.-L. Zhu, G .
a!LL
Zhu, Z. Zimmerman, T. Zipp, G.G. Zirange, M.B . Zirpurua, J.M. Zolfigol, M.A. Zou, H. Zubaklha, P.K. Zubairi, Md.0. Zuercher, W.J. Zuo, B.J. Zupan, M.
Compendium of Organic Synthetic Methods, Vol 10
294
040,055, 146
199 189 007 087, 329 177,214, 341 154 221 161 123 054 221 158 087 079 023 298 095,099 035,073 041, 153, 315, 316 158 016 286 348 113 141, 326 268 011, 149 045 337 247 325 120, 130
Authors
