Kinetic Resolution of Amines by a Nonenzymatic Acylation Catalyst

Authors


  • We thank Michael M.-C. Lo, Dr. J. Craig Ruble, and Beata Tao for helpful discussions and preliminary studies, and we also thank Dr. George P. Luke (ARIAD Pharmaceuticals, Inc.) for providing the primary amine illustrated in entry 8 of Table 1. Support has been provided by Bristol-Myers Squibb, Merck, the National Institutes of Health (National Institute of General Medical Sciences, R01-GM57034), Novartis, Pfizer, and Pharmacia.

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.

Ancillary