Highly efficient kinetic resolution of beta-halohydrins catalyzed by a chiral 1,2-diamine.

Abstract

Kinetic resolution of racemic beta-halohydrins has been achieved by reaction with benzoyl chloride in the presence of a catalytic amount (0.3 mol%) of a chiral diamine combined with diisopropylethylamine to afford the corresponding benzoates and unreacted beta-halohydrins in good to excellent enantioselectivities. The benzoate can be converted to the corresponding allylic benzoate without loss of optical purity by treatment with (1,5-diazabicyclo[4.3.0]non-5-ene).