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

Olaf Cussó, Isaac Garcia-Bosch, Xavi Ribas, Julio Lloret-Fillol and Miquel Costas*

*QBIS ResearchGroup, Institut de Química Computacional i Catàlisi (IQCC) and Departament de Química, Universitat de Girona, Campus Montilivi, Girona E-17071, Catalonia, Spain, Email: miquel.costasudg.edu

O. Cussó, I. Garcia-Bosch, X. Ribas, J. Lloret-Fillol, M. Costas, J. Am. Chem. Soc., 2013, 135, 14871-14878.

DOI: 10.1021/ja4078446 (free Supporting Information)


Abstract

A non-heme iron complex catalyzes highly enantioselective epoxidation of olefins with H2O2 in the presence of catalytic amounts of carboxylic acid additives. Ligand and carboxylic acid synergistically cooperate 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.

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Key Words

Epoxidation, Hydrogen Peroxide


ID: J48-Y2013