Organic Chemistry Portal



Asymmetric Organocatalytic Epoxidation of α,β-Unsaturated Aldehydes with Hydrogen Peroxide

Mauro Marigo, Johan Franzén, Thomas B. Poulsen, Wei Zhuang, and Karl Anker Jřrgensen*

*Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark, Email:

M. Marigo, J. Franzen, T. B. Poulsen, W. Zhuang, K. A. Jorgensen, J. Am. Chem. Soc., 2005, 127, 6284-6289.

DOI: 10.1021/ja051808s


A chiral bisaryl-silyl-protected pyrrolidine acts as a very selective epoxidation organocatalyst using simple oxidation agents. The scope of the reaction is demonstrated by the formation of optically active α,β-epoxy aldehydes in high yields and enantioselectivities. The asymmetric epoxidation reactions proceed also under environmental friendly reaction conditions in, for example, water mixtures of alcohols.

see article for more examples

Key Words

Epoxidation, Organocatalysis, Epoxy Aldehydes, Hydrogen Peroxide

ID: J48-Y2005-2340