Applications of biotransformations in organic synthesis: preparation of enantiomerically pure esters of cis- and trans-epoxysuccinic acid

Abstract

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,3RS)-2hydroxy-3-(4-methylphenyl)sulfonyloxybutanoic acid], followed by esterification with 2-methylpropanol and oxirane formation.