(S)-Proline-Derived Catalysts for the Acylative Kinetic Resolution of Alcohols: A Remote Structural Change Allows a Complete Selectivity Switch

Abstract

A systematic preliminary study has identified a suite of catalysts, all readily prepared and derived from (<i>S</i>)-proline, which differ by a remote substituent only. If this substituent is capable of hydrogen-bond donation the catalyst will promote the resolution of secondary alcohols with the opposite sense of enantiodiscrimination to that observed when the substituent is capable of accepting hydrogen bonds.