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Asymmetric Epoxidation with H 2 O 2 by Manipulating the Electronic Properties of Non-heme Iron Catalysts

2013; American Chemical Society; Volume: 135; Issue: 39 Linguagem: Inglês

10.1021/ja4078446

1943-2984

Olaf Cussó, Isaac Garcia‐Bosch, Xavi Ribas, Julio Lloret‐Fillol, Miguel Costas,

Porphyrin and Phthalocyanine Chemistry

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.