Surprising stereoselectivity in the Payne epoxidation of terpinen-4-ol with acetonitrile/hydrogen peroxide

Abstract A surprisingly high level of cis -stereoselectivity in the Payne epoxidation has been identified with the homoallylic alcohol, terpinen-4-ol. Very high efficiencies for hydrogen peroxide are realized under mild conditions. The necessity for peroxyimidic acid stabilization by solvent is replaced by coordination to the directing hydroxyl function, resulting in dramatically improved space yields at up to the one kilogram scale.