STEREOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE E-HOMOALLYL AND Z-HOMOALLYL ALCOHOLS FROM EPOXIDES

被引：5

作者：

OKUMA, K ^{[1
]}

TANAKA, Y ^{[1
]}

OHTA, H ^{[1
]}

MATSUYAMA, H ^{[1
]}

机构：

[1] TOKYO METROPOLITAN UNIV,FAC SCI,DEPT CHEM,HACHIOJI,TOKYO 19203,JAPAN

来源：

HETEROCYCLES | 1993年 / 36卷 / 01期

关键词：

D O I：

10.3987/COM-92-6213

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active E- and Z-homoallyl alcohols were prepared by Wittig and Warren olefination starting from optically active 3-hydroxyalkyltriphenylphosphonium salts, which were obtained by the reaction of epoxides with methylenetriphenylphosphorane and dibenzoyltartric acid followed by optical resolution.

引用

页码：37 / 40

页数：4

共 15 条

[1] THE STEREOCONTROLLED HORNER-WITTIG REACTION - SYNTHESIS OF DISUBSTITUTED ALKENES
BUSS, AD
WARREN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11): : 2307 - 2325
[2] SYNTHESIS OF (RECIFEIOLIDE) (R)-TRANS-11-HYDROXY-8-DODECENOIC ACID LACTONE
GERLACH, H
OERTLE, K
THALMANN, A
[J]. HELVETICA CHIMICA ACTA, 1976, 59 (03) : 755 - 760
[3] GOSNEY I, 1979, ORGANOPHOSPHORUS REA, pCH2
[4] OPTICALLY-ACTIVE ALLYLSILANES .4. ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES WITH AN OPTICALLY-ACTIVE ALLYLSILANE
HAYASHI, T
KONISHI, M
KUMADA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (02) : 281 - 282
[5] TRANS STEREOSELECTIVITY IN THE REACTION OF (4-CARBOXYBUTYLIDENE) TRIPHENYLPHOSPHORANE WITH AROMATIC-ALDEHYDES
MARYANOFF, BE
DUHLEMSWILER, BA
[J]. TETRAHEDRON LETTERS, 1981, 22 (42) : 4185 - 4188
[6] THE WITTIG OLEFINATION REACTION AND MODIFICATIONS INVOLVING PHOSPHORYL-STABILIZED CARBANIONS - STEREOCHEMISTRY, MECHANISM, AND SELECTED SYNTHETIC ASPECTS
MARYANOFF, BE
REITZ, AB
[J]. CHEMICAL REVIEWS, 1989, 89 (04) : 863 - 927
[7] MACROLIDES - RECENT PROGRESS IN CHEMISTRY AND BIOCHEMISTRY
MASAMUNE, S
BATES, GS
CORCORAN, JW
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (09): : 585 - 607
[8] MIKAMI K, 1991, SYNTHESIS-STUTTGART, P594
[9] CATALYTIC ASYMMETRIC GLYOXYLATE ENE REACTION - A PRACTICAL ACCESS TO ALPHA-HYDROXY ESTERS IN HIGH ENANTIOMERIC PURITIES
MIKAMI, K
TERADA, M
NAKAI, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) : 3949 - 3954
[10] ASYMMETRIC ALLYLATION OF PROCHIRAL ALDEHYDES WITH A NEW ENANTIOSELECTIVE ALLYLATING AGENT PREPARED FROM STANNOUS TRIFLATE, A CHIRAL DIAMINE, AND ALLYLDIALKYLALUMINUM
MUKAIYAMA, T
MINOWA, N
ORIYAMA, T
NARASAKA, K
[J]. CHEMISTRY LETTERS, 1986, (01) : 97 - 100

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