Asymmetric Epoxidation with H₂O₂ by Manipulating the Electronic Properties of Non-heme Iron Catalysts

A non-heme iron complex that catalyzes highly enantioselective epoxidation of olefins with H2O2 is described. Improvement of enantiomeric excesses is attained by the use of catalytic amounts of carboxylic acid additives. Electronic effects imposed by the ligand on the iron center are shown to synergistically cooperate with catalytic amounts of carboxylic acids in promoting efficient O–O cleavage and creating highly chemo- and enantioselective epoxidizing species which provide a broad range of epoxides in synthetically valuable yields and short reaction times.