A Stereoelectronic Basis for the Kinetic Resolution of N-Heterocycles with Chiral Acylating Reagents

摘要

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 using easily prepared reagents. A transition state model to rationalize the stereochemical outcome of this kinetic resolution is also proposed.