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Highly Enantioselective, Catalytic Epoxidation of Trisubstituted Olefins

Bridget D. Brandes and Eric N. Jacobsen

*Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, Email:

B. D. Brandes, E. N. Jacobsen, J. Org. Chem., 1994, 59, 4378-4380.

DOI: 10.1021/jo00095a009


Chiral (salen)Mn(III) complexes are highly selective catalysts for the asymmetric epoxidation of several cyclic and acyclic trisubstituted olefins. Addition of a catalytic amount of pyridine N-oxide derivatives has a slight beneficial effect on enantioselectivity, reaction rate and product yield.

see article for more examples

Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane

E. N. Jacobsen, W. Zhang, A. R. Muci, J. R. Ecker, L. Deng, J. Am. Chem. Soc., 1991, 113, 7063-7064.

Key Words

Jacobsen Epoxidation, Manganese, Bleach

ID: J42-Y1994-540