Starting from correspongding olefins, eight chiral β-aminoalcohols were synthesized by Sharpless asymmetric dihydroxylation and applied in the organocatalytic asymmetric epoxidation of α,β-enones. The effects of the amount of catalysts, the structure of catalysts, oxidant, solvent and reaction temperature on enantioselectivity were also studied. When the amount of catalyst was 30 mol% relative to α,β-enones, tert-butyl hydroperoxide (TBHP) as oxidant, hexane as a solvent at room temperature, (1S,2R)-1,2-diphenyl- 2-(N-methyl)aminoethanol (3) has been successfully applied as catalyst in asymmetric epoxidation of α,β-enones with the yield up to 84% and enantiomeric excesses up to 70%.

Key words: α,β-enone, chiral β-aminoalcohol, asymmetric catalysis, asymmetric epoxidation