Chiral amine salts were applied to catalyze the asymmetric epoxidation of α,β-enones. It was found that a variety of chiral amines and oxidants affected the enantioselectivity of the reaction respectively. The results showed that the optical yield reached up to 84% ee when 9-amino(9-deoxy)epicinchonine (A6) was used to catalyze the asymmetric epoxidation of α,β-unsaturated ketones. Meanwhile, the β-cyclodextrin- modified chiral amine salt also exhibited the chiral inducibility in asymmetric epoxidation of chalcone.

Key words: α,β-enone, asymmetric epoxidation, chiral amine, cinchona alkaloid, β-cyclodextrin