A Facile Chemoenzymatic Route to Optically Active 4, 5-Disubstituted-2E-hexenoate Derivatives. I

Abstract

The reaction of (±) methyl 4, 5-trans-epoxy-2E-hexenoate (2) with aromatic nucleophiles having an electrondonating group in the presence of BF₃·Et₂O gave the 4, 5-anti-5-hydroxy-4- or/and 2, 5-anti-5-hydroxy-2-substituted products. The 5-acetates of the 4, 5-anti-4-substitution products were subjected to enantioselective hydrolysis with lipase to provide the optically acitive 4, 5-disubstituted 2-hexenoate derivatives.