Chiral poisoning in the kinetic resolution of allylic alcohols

Abstract

Recently, hydrogenations of allylic alcohols using ruthenium catalysts with enantiomerically pure phosphines, such as ( R)-BINAP were reported to be useful for the kinetic resolution of cyclic allylic alcohols. These kinetic resolutions can also be effected using racemic BINAP and preferentially deactivating one enantiomer of the catalyst with an enantiomerically pure chiral poison. Poisoning of racemic (BINAP)-RuCl 2 (dmf) x with (1 R,2 S)-ephedrine provided ( R)-2-cyclohexenol in 93% ee at 72% conversion.