Halogenative kinetic resolution of β-aryloxy cyclic alcohols: chiral BINAP-mediated SN2 displacement of hydroxy groups by chlorides with inversion of stereochemistry

A series of optically active cyclic trans-β-aryloxy alcohols have been obtained by non-enzymatic kinetic resolution of the corresponding racemic aryloxy cyclic alcohols using commercially available (S)-BINAP and NCS by S_N2 halogenation of a hydroxy group. The product, cis-β-aryloxy chlorides, was also obtained in optically active form with inversion of the stereochemistry.