Selective enzymatic transformations of itaconic acid derivatives: An access to potentially useful building blocks

Article abstract of DOI:10.1016/S0040-4020(01)81120-0

Hydrolytic enzymes regioselectively catalyze the hydrolysis of diethyl itaconate 5a to the monoester 5c and opening of itaconic anhydride 6 to the regioisomeric monoester 5b that was transformed into the hydroxy esters 2. This was used for the synthesis of β-methylene-γ-butyrolactone 7 and of the racemic epoxyalcohol 3, that was resolved by a highly enantioselective Pseudomonas fluorescens lipase-catalyzed transesterification into (S)-3 and (S)-8 (90 and 86% ee, respectively).