Highly Diastereoselective Epoxidation of α,β-Unsaturated Carbonyl Compounds Using Sodium Peroxide

A novel epoxidation method is described using sodium peroxide as an oxidant. A wide variety of alpha,beta-unsaturated carbonyl compounds, particularly (E)-chalcones were oxidized to the corresponding epoxides in good to excellent yields. On the other hand, all reactions underwent smoothly in short reaction times, and the high reactivity of sodium peroxide was noticed for the first time toward the epoxidation of alpha,beta-unsaturated carbonyl compounds, and kinetically proved. In all the cases, the epoxidation proceeded diastereospecifically.