Lipase catalyzed transesterification of 2-substituted 3-hydroxy esters

Abstract

Kinetic resolution of 2-substituted 3-hydroxy esters was examined by lipase PS catalyzed transesterification using vinyl acetate as an acyl donor. Resolution of (±)-syn- and -anti-1a, -1e possessing a small methyl group at the C-3 position was accomplished enantioselectively. The outcome of the resolution seems to be related to the differences in size of the substituents at the stereocenter bearing a secondary hydroxy group. Chirality 10:693–698, 1998. © 1998 Wiley-Liss, Inc.