Enzyme-mediated enantioselective hydrolysis of cyclic carbonates bearing an unsaturated substituent

A new method for the preparation of optically active five-membered cyclic carbonates bearing an unsaturated substituent via an enzymatic reaction is described. In the examination of the regiospecific recognition of PPL, dl-(E)-4-(1-octenyl)-1,3-dioxolan-2-one is hydrolyzed with higher enantioselectivity. The reaction is also applicable to the racemic (E)-4-[2-(alkoxycarbony)ethenyl]-1,3-dioxolane-2-one, a useful α,β-unsaturated ester in organic syntheses. Introducing the isopropyl group to the ester moiety affords the highest enantioselectivity although the ester group is located at a remote position from the asymmetric carbon.