Kinetic resolution via semipinacol rearrangement of α-hydroxy epoxides: a new method for asymmetric synthesis of α-hydroxy epoxides and β-hydroxy ketones containing an α-quaternary carbon

Abstract

A new method for the enantioselective preparation of β-hydroxy ketones containing a stereogenic quaternary carbon center and tertiary α-hydroxy epoxides has been developed on the basis of kinetic resolution of racemic tertiary α-hydroxy epoxide via semipinacol rearrangement using the chiral catalyst Ti-[( R)/( S)-BINOL] 2. The effect of the structure of the migrating group on the enantioselectivity of the reaction is also discussed.