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

D. Subhas Bose; A. V. Narsimha Reddy; Sanjay W. Chavhan

doi:10.1055/s-2005-870021

PAPER

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

D. Subhas Bose*, A. V. Narsimha Reddy, Sanjay W. Chavhan
Organic Chemistry Division III, Fine Chemical Laboratory, Indian Institute of Chemical Technology, Hyderabad, 500 007, India
Fax: +91(40)27160387; e-Mail: dsb@iictnet.org; e-Mail: dsb@iict.res.in;

Abstract

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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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