A series of enantiopure β-amino alcohols were synthesized from the corresponding diols produced by Sharpless asymmetric dihydroxylation, cyclization of diols, azide opening of epoxides, and catalytic hydrogenation of the resulting azido alcohols. Factors to affect the azide opening of the epoxides were examined. Overall yields from epoxides to amino alcohols were 89%～94%, while enantiomeric excess values of β-azido alcohols and β-amino alcohols were up to 90%～99%.

Key words: asymmetric synthesis, chiral β-amino alcohol, chiral vicinal diol, chiral β-azido alcohol, asymmetric dihydroxylation