A FACILE SYNTHESIS OF OPTICALLY-ACTIVE GAMMA-CYANOALLYLIC ALCOHOLS USING ASYMMETRIC HYDROCYANATION OF ALPHA,BETA-ALKENYL ALDEHYDES FOLLOWED BY STEREOSPECIFIC [3.3]SIGMATROPIC CHIRALITY TRANSFER OF THE CYANOHYDRIN ACETATES

被引：31

作者：

ABE, H ^{[1
]}

NITTA, H ^{[1
]}

MORI, A ^{[1
]}

INOUE, S ^{[1
]}

机构：

[1] UNIV TOKYO, DEPT SYNTHET CHEM, BUNKYO KU, TOKYO 113, JAPAN

来源：

CHEMISTRY LETTERS | 1992年 / 12期

关键词：

D O I：

10.1246/cl.1992.2443

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Optically active gamma-cyanoallylic alcohols were synthesized by using asymmetric hydrocyanation of alpha, beta-alkenyl aldehydes catalyzed by peptide-titanium complex to give alpha-cyanoallylic alcohols (cyanohydrins) with high optical yields followed by palladium complex catalyzed [3.3]sigmatropic chirality transfer of the corresponding acetates.

引用

页码：2443 / 2446

页数：4

共 12 条

[1] ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF SOME ALDEHYDES BY CHIRAL TITANIUM SCHIFFS BASE COMPLEXES
HAYASHI, M
MIYAMOTO, Y
INOUE, T
OGUNI, N
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (24) : 1752 - 1753
[2] A HIGHLY EFFICIENT SYNTHESIS OF OPTICALLY PURE GAMMA-IODO ALLYLIC ALCOHOLS AND THEIR CONVERSION INTO VARIOUS OPTICALLY-ACTIVE ALLYLIC ALCOHOLS
KITANO, Y
MATSUMOTO, T
WAKASA, T
OKAMOTO, S
SHIMAZAKI, T
KOBAYASHI, Y
SATO, F
MIYAJI, K
ARAI, K
[J]. TETRAHEDRON LETTERS, 1987, 28 (50) : 6351 - 6354
[3] ENANTIOSELECTIVE ADDITION-REACTION OF TRIMETHYLSILYL CYANIDE WITH ALDEHYDES USING A CHIRAL TIN(II) LEWIS ACID
KOBAYASHI, S
TSUCHIYA, Y
MUKAIYAMA, T
[J]. CHEMISTRY LETTERS, 1991, (04) : 541 - 544
[4] PALLADIUM-CATALYZED REARRANGEMENT OF ALPHA-CYANOALLYLIC ACETATES APPLICATION TO A NEW SYNTHETIC METHOD FOR FURANS
MANDAI, T
HASHIO, S
GOTO, J
KAWADA, M
[J]. TETRAHEDRON LETTERS, 1981, 22 (23) : 2187 - 2190
[5] ASYMMETRIC HYDROCYANATION OF ALDEHYDES USING CHIRAL TITANIUM REAGENTS
MINAMIKAWA, H
HAYAKAWA, S
YAMADA, T
IWASAWA, N
NARASAKA, K
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (12) : 4379 - 4383
[6] PEPTIDE-METAL COMPLEX AS AN ASYMMETRIC CATALYST - A CATALYTIC ENANTIOSELECTIVE CYANOHYDRIN SYNTHESIS
MORI, A
NITTA, H
KUDO, M
INOUE, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (34) : 4333 - 4336
[7] MORI A, 1991, SYNLETT, P563
[8] NITTA H, IN PRESS J AM CHEM S
[9] OHNO H, IN PRESS J ORG CHEM
[10] Overman, 1984, ANGEW CHEM, V96, P565

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