Kinetic resolution of racemic beta-halohydrinshas 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 correspo
nding benzoates and unreacted beta-halohydrins in good to excellent enantio
selectivities. The benzoate can be converted to the corresponding allylic b
enzoate without loss of optical purity by treatment with (1,5-diazabicyclo[
4.3.0]non-5-ene).