A FACILE CHEMOENZYMATIC ROUTE TO ENANTIOMERICALLY PURE 4, 5-DISUBSTITUTED-2-HEXENOATE DERIVATIVES

Abstract

The reaction of 4, 5-epoxy-2-hexenoate 2__- and various nucleophiles in the presenece of BF₃.Et₂0 predominantly gave the (4, 5)-5-hydroxy-4-substituted compounds. Among them, (±)-(4, 5)-anti-5-hydroxy-4-thiophenoxy ester 17 was enantioselectively esterified with acylating reagent in the presence of lipase "PL 266" from Alcaligenes sp. to provide the (4S, 5R)-5-acetoxy ester 20 and the (4R, 5S)-17 quantitatively.