Diastereoselectivity in the Epoxidation of Substituted Cyclohexenes by Dimethyldioxirane(1)(,)(2).

Three series of compounds based on the cyclohexene framework have been epoxidized by dimethyldioxirane. A pronounced dependence of epoxide diastereoselectivity on substituent has been observed. In addition there is a solvent influence on this stereoselectivity. The results have been explained by invoking steric, H-bonding, and dipole-dipole influences on the epoxide stereochemistry.