Highly enantioselective osmium dihydroxylation of unsubstituted allyl N-phenylcarbamate using AD-mix reagents

A prominent effect of the phenylcarbamoyl protecting group on the asymmetric dihydroxylation (AD) reaction was confirmed in both of the reactions of allyl N-phenylcarbamate with AD-mix-α and -β, bringing about excellent enantioselectivity (>99% ee) to give (R)- and (S)-glycerol 1-(N-phenylcarbamate) in quantitative yields, respectively.