Hydrolytic Kinetic Resolution of α-Naphthyl Glycidyl Ether: A Practical Access to Highly Enantioselective β-Adrenergic Blocking Agents

Abstract

Kinetic resolution of (±)-naphthyl glycidyl ether using 0.5 mol% (R,R)-salen Co(III)OAc and water (0.55 equiv) provided enantiomerically pure naphthyl glycidyl ether and 1-naphthylglycerol derivatives with high enantiomeric excess. Application of this approach to highly enantioenriched (S)-naftopidil and (S)-propranolol is described.

Key words

naphthyl glycidyl ether - hydrolytic kinetic resolution - naftopidil - propranolol - terminal epoxide

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