Enzymatic Hydrolysin in Organic Solvents for Kinetic Resolution of Water-Insoluble α-Acyloxy Esters with Immobilized Lipases

Abstract

Enantioselective hydrolysis of water-insoluble α-acyloxy esters, (±)-5 and (±)-6, was carried out using lipases immobilized with Celite or a synthetic prepolymer (ENTP-4000 or ENT-4000) in a water-saturated organic solvent to produce chiral intermediates, (2S, 3S)-5 and (2S, 3R)-4, for the synthesis of diltiazem hydrochloride 1 and (-)-indolmycin 2, respectively. Furthermore, enantioselective hydrolysis of (±)-6 using lipid-lipase aggregates in water-saturated organic solvent was also found to give (2S, 3R)-4.