Stereoselective synthesis of (R)-glycidyl butyrate from racemic glycidyl butyrate or epichlorohydrin via hydrolytic kinetic resolution

摘要

The differences of (R)-glycidyl butyrate synthesis via hydrolytic kinetic resolution of glycidyl butyrate directly or regioselective opening epichlorohydrin as key steps by using Jacobsen's hydrotic kinetic resolution are compared. In the view of separation problem, it is hard to get the pure (R)-glycidyl butyrate by kinetic resolution of glycidyl butyrate directly. Via kinetic resolution of epichlorohydrin, treatment with butyric acid in the presence of CrCl_3 and then epoxidation with NaOH, the total yield of 38.5% and optical purity of 99% are obtained.