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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: kajchem.au.dk

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

DOI: 10.1021/ja051808s (free Supporting Information)


Abstract

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.

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Key Words

Epoxidation, Organocatalysis, Epoxy Aldehydes, Hydrogen Peroxide


ID: J48-Y2005-2340