Organocatalysis of asymmetric epoxidation by iminium salts using sodium hypochlorite as the stoichiometric oxidant

Iminium salts can provide high selectivity and high efficiency when used as organocatalysts for asymmetric epoxidation. For this purpose, they are normally used in conjunction with Oxone as the stoichiometric oxidant. Oxone, however, has limited stability, is insoluble in most organic solvents, is atom-inefficient, and produces considerable inorganic residue as the by-product of oxidation. In this paper we report for the first time the development of a reaction system driven by sodium hypochlorite as the stoichiometric oxidant.