Lipase-catalyzed chemo- and enantioselective acetylation of 2-alkyl/aryl-3-hydroxypropiophenones

The chemo- and enantioselective capabilities of porcine pancreatic lipase ( PPL) in tetrahydrofuran, and Candida rugosa lipase (CRL) in diisopropyl eth er have been investigated for the acetylation of racemic 2-alkyl/aryl-3-hyd roxypropiophenones, which are important precursors in the synthesis of biol ogically active chromanones and isoflavanones. A highly chemoselective acet ylation of primary hydroxy group in preference to phenolic hydroxy group le ading to the formation of enantiomerically enriched monoacetates has been o bserved. (C) 2001 Elsevier Science Ltd. All rights reserved.