PRODUCTION OF OPTICALLY ACTIVE PROPARGYL ALCOHOL

摘要

PURPOSE:To simply obtain an optically active propargyl alcohol a synthetic intermediate for an omega side chain of prostaglandin derivative, having excellent optical purity, by reacting a specific (RS)-propargyl alcohol compound with an acylating agent in the presence of an enzyme. CONSTITUTION:An (RS)-propargyl alcohol compound of formula I [R<1> and R<2> are each H or a 1-3C alkyl; R<3> is (substituted) phenyl, a 1-8C alkyl or a 5-8C cycloalkyl] [e.g. (3RS)-3-hydroxy-4-phenoxy-1-butyne] is reacted with an acylating agent of the formula R<4>COOR [R<4> is a 1-10C alkyl or a (substituted) phenyl ; R is an alkyl or an alkenyl] (e.g. isopropenyl acetate) in the presence of an enzyme (e.g. lipase PS) derived from a bacterium belonging to the genus Pseudomonas to simply give the objective optically active O-acylpropargyl alcohol compound of formula II (* is optically active) having excellent optical purity useful as a synthetic intermediate for a physiologically active substance.