Diastereoselectivity in the epoxidation of substituted cyclohexenes by dimethyldioxirane

The diastereoselectivity and chemoselectivity in the reactions of dimethyldioxirane with cyclohexene derivatives were examined. Three series of compounds with cyclohexene framework were epoxidized by dimethyldioxirane. The results showed the influence of substituent and solvent on epoxide diatereoselectivity. These were explained in terms of steric, H-bonding and dipole-dipole factors.