Generation of near-enantiopure α-alkyl α-formyl α-hydroxy ketones/esters and their interception with ethoxycarbonylmethylenetriphenylphosphorane

被引：8

作者：

Bhatia, GS ^{[1
]}

Lowe, RF ^{[1
]}

Stoodley, RJ ^{[1
]}

机构：

[1] UMIST, Dept Chem, Manchester M60 1QD, Lancs, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 50期

基金：

英国工程与自然科学研究理事会;

关键词：

carbohydrates; cleavage reactions; epoxides; Wittig reactions;

D O I：

10.1016/S0040-4039(98)02011-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two protocols for the generation of the (R)-enantiomers of alpha-alkyl alpha-formyl alpha-hydroxy ketones/esters in states of high enantiomeric purity are developed; the formyl functions of such compounds undergo Wittig condensations with ethoxycarbonylmethylenetriphenylphosphorane in dimethyl sulfoxide to afford the corresponding alkenes with high (E)-stereoselectivities and with e.e.s of 91-99%. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：9245 / 9248

页数：4

共 5 条

[1]

Bhatia GS, 1997, CHEM COMMUN, P1981

[2]

FIANDOR J, 1985, SYNTHESIS-STUTTGART, P1121

[3] SYNTHETIC STUDIES TOWARDS PSEUROTIN-A .3. SYNTHESIS OF A RELATED HIGHLY FUNCTIONALIZED GAMMA-LACTONE [J].