Asymmetric dihydroxylation of 1, 1-disubstituted and 1, 3-disubstituted allenes can be used to synthesize chiral α-hydroxy ketones. We have also obtained α, α′-dihydroxy ketones with high enantioselectivity from 1, 3-disubstituted allenes. Low conversion of the dihydroxylation of chiral allenes can be used as a kinetic resolution of sterically hindered allenes.