A facile and convenient chemoenzymatic synthesis of optically active O-(4-methoxyphenyl)-glycidol and 1,2-diacyl-sn-glycerol

Abstract

A convenient preparation of the (R)- and (S)-enantiomers of O-(4-methoxyphenyl)-glycidol by a one-pot reduction of ketone 3 and in situ lipase mediated resolution is described. Activated moist aluminium oxide in the presence of Pseudomonas cepacia lipase immobilized on ceramic particles (PS-C) has been found effective for the transesterification leading to a high degree of enantioselectivity. These chiral glycidols were further used as a chiral precursor for the synthesis of biologically important 1,2-O-diacyl-sn-glycerol under mild reaction conditions. The present method is facile for the synthesis of chiral glycidols in high enantioselectivity when compared to the previously reported methods. © 2005 Elsevier Ltd. All rights reserved.