APPLICATIONS OF BIOTRANSFORMATIONS IN ORGANIC-SYNTHESIS - PREPARATION OF ENANTIOMERICALLY PURE ESTERS OF CIS-EPOXYSUCCINIC AND TRANS-EPOXYSUCCINIC ACID

被引：9
|
作者：
CROUT, DHG
GAUDET, VSB
HALLINAN, KO
机构：
[1] Department of Chemistry, University of Warwick
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 07期
关键词：
D O I：
10.1039/p19930000805
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chemical and enzymatic procedures have been investigated for the resolution of esters of trans-epoxysuccinic acid (trans-oxirane-2,3-dicarboxylic acid). A successful resolution was achieved by transesterification of the diethyl ester against heptanol catalysed by the lipase from Rhizopus javanicus. Asymmetrization of cis-epoxysuccinic acid was achieved by enantioselective and regiospecific hydrolysis of the,racemic diethyl ester of 2-(toluene-p-sulfonyloxy)tartaric acid [(2RS,2RS)-2-hydroxy-3-(4-methylphenyl)sulfonyloxybutanoic acid], followed by esterification with 2-methylpropanol and oxirane formation.
引用
收藏
页码：805 / 812
页数：8
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