Halogenative kinetic resolution of β-amido alcohols: Chiral BINAP-mediated S<inf>N</inf>2 displacement of hydroxy groups by chlorides with inversion of stereochemistry

A series of optically active cyclic trans-β-amido alcohols were obtained by the non-enzymatic kinetic resolution of the corresponding racemic amido alcohols using commercially available (S)-BINAP and NCS by SN2 halogenation of the hydroxy group. The product, cis-β-amido chloride, was also obtained in optically active form with an inversion of stereochemistry. © 2010 Elsevier Ltd. All rights reserved.