A simple and efficient protocol for epoxidation of olefins using dimethyldioxirane

The reaction of a series of monoterpenic olefins and Δ4-octalins with dimethyldioxirane led to the corresponding epoxides in excellent yields. Remarkable diastereoselectivity was observed for the Δ4-octalins. The procedure consists simply in stirring the substrate, NaHCO3 and acetone, at 0°C, with dropwise addition of an aqueous solution of oxone.