Kinetic Resolution of Amines by a Nonenzymatic Acylation Catalyst

Abstract

A planar-chiral DMAP derivative, in conjunction with a readily available, novel acylating agent, effects the kinetic resolution of α-arylamines, a biologically important class of compounds, with a selectivity factor of up to 27 (see scheme). The catalyst used, PPY*, is the first effective nonenzymatic catalyst for the enantioselective acylation of amines. DMAP=4-dimethylaminopyridine.