BIOCATALYTIC RESOLUTIONS OF SULFINYLALKANOATES - A FACILE ROUTE TO OPTICALLY-ACTIVE SULFOXIDES

被引：25

作者：

BURGESS, K

HENDERSON, I

HO, KK

机构：

[1] Department of Chemistry, Rice University, Houston, Texas 77251

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 04期

关键词：

D O I：

10.1021/jo00030a044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two methods are presented for kinetic resolutions of compounds containing ester and sulfoxide functionalities (sulfinylalkanoates). In the first a crude lipase preparation from Pseudomonas sp. (K10) mediates enantioselective hydrolysis of these esters in an aqueous environment. The second method uses the same lipase preparation to promote enantioselective transesterifications with alcohols in hexane. Both procedures are suitable for preparation of sulfinylalkanoates where the ester and sulfoxide groups are separated by one or two methylene units (sulfinylacetates and sulfinylpropanoates) but compounds with three methylene "spacer groups" (sulfinylbutanoates) are not substrates for the lipase under either set of conditions.

引用

页码：1290 / 1295

页数：6

共 49 条

[1] SYNTHESIS OF BOTH ENANTIOMERS OF OPTICALLY PURE SATURATED AND ALPHA,BETA-UNSATURATED GAMMA-SUBSTITUTED GAMMA-LACTONES FROM CHIRAL SULFOXIDES - X-RAY MOLECULAR-STRUCTURE OF (3R,4S)-4-METHYL-4-TERT-BUTYL-3-(PARA-TOLYLTHIO)BUTANOLIDE AND OF (3R,4R)-4-(CYCLOHEX-1-ENYL)-4-METHYL-3-(PARA-TOLYLTHIO)BUTANOLIDEL [J].