Stereoelectronic basis for the kinetic resolution of N-heterocycles with chiral acylating reagents

Abstract

The kinetic resolution of N-heterocycles with chiral acylating agents reveals a previously unrecognized stereoelectronic effect in amine acylation. Combined with a new achiral hydroxamate, this effect makes possible the resolution of various N-heterocycles by using easily prepared reagents. A transition-state model to rationalize the stereochemical outcome of this kinetic resolution is also proposed.

Keywords: N-heterocycles; hydroxamic acid; kinetic resolution; stereoelectronic effects; synthetic methods.