Highly stereoselective epoxidation of O-protected 3-hydroxy-1-nitroalkenes

The diastereoselectivity of the nucleophilic epoxidation of O-protected 3-hydroxy-1-nitroalkenes was investigated. Epoxidation of the O-protected 3-hydroxy-1-nitroalkenes was highly stereoselective, giving rise to the anti isomer. The resulting nitroepoxides have been transformed into nitroaldols through hydrogenation. The nucleophilic epoxidation of nitroalkenes was found to be irreversible. Models to explain the observed stereoselectivities are proposed.