Oxidative Kinetic Resolution of Secondary Alcohols

Significance

A highly enantioselective organocatalytic oxidative kinetic resolution of ­racemic secondary alcohols using chiral 2-aza-adamantane N-oxyls (AZADOs) as catalyst was disclosed by the authors. 4-Aryl-1-alkyl-AZADOH (see Scheme) exhibits superior catalytic activity and high enantioselectivity in the kinetic resolution of α-substituted cyclopentanol and cyclohexanols, and high k _rel values (up to 82.2) were obtained. The working hypothesis in the paper suggests both benzyl group and butyl group in the catalyst play an important role in the discrimination of racemic alcohols during the course of the oxidation.