Resolution of α-methylene-β-hydroxy esters catalyzed by free and immobilized Pseudomonas sp lipase

Kinetic resolutions of alpha-methylene-beta-hydroxy esters (Baylis-Hillman products) have been performed via enzymatic enantioselective transesterification with Pseudomonas sp. lipase (PSL), free or immobilized in poly(ethylene) oxide (PEO), silica gel and montmorillonite K10. under different reaction conditions. The corresponding (R)-(+)-acetates from alkyl-substituted racemic alcohols were obtained with e.e. >99% and excellent to moderate conversions using the PSL/PEO system and vinyl acetate as acylating agent, in hexane. A naphthyl-substituted hydroxy ester was inert under these experimental conditions. (C) 2003 Elsevier Ltd. All rights reserved.