E/Z DIASTEROSELECTIVE ENZYMATIC-HYDROLYSIS OF ESTERS AND DIESTERS

With porcine liver esterase the α,β‐unsaturated diester 1 can be hydrolyzed selectively at the ester group in the Z position relative to the carbonyl group. The further saponification to give the dicarboxylic acid is achieved with aqueous NaOH. However, even under drastic conditions, 1 cannot be hydrolyzed in one step by either bases or acids with retention of the β‐lactam ring. (Figure Presented.) Copyright © 1993 by VCH Verlagsgesellschaft mbH, Germany