Axially Chiral Analogues of 4-(Dimethylamino)pyridine: Novel Catalysts for Nonenzymatic Enantioselective Acylations

Abstract

A concise seven-step synthesis of atropisomeric 3-aryl analogues of DMAP from 4-pyridone 8 has been developed. A representative compound of this class, biaryl (+/-)-15, has been resolved using CSP HPLC and shown to be an efficient nucleophilic catalyst for kinetic resolution of a series of secondary alcohols on both an analytical and preparative scale (stereoselectivity factors, s = 8.9-29).