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Organocatalysis with a Fluorous Tag: Asymmetric Reduction of Imines with Trichlorosilane Catalyzed by Amino Acid-Derived Formamides

Andrei V. Malkov,* Marek Figlus, Sigitas Stončius and Pavel Kočovský*

*Department of Chemistry, WestChem, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, Scotland, United Kingdom, Email:,

A. V. Malkov, M. Figlus, S. Stončius, P. Kočovský, J. Org. Chem., 2007, 72, 1315-1325.

DOI: 10.1021/jo062215i

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Asymmetric reduction of ketimines with trichlorosilane can be catalyzed by N-methylvaline-derived Lewis-basic formamides with high enantioselectivity and low catalyst loading at room temperature in toluene. Appending a fluorous tag to the catalyst simplifies the isolation procedure and allows the catalyst to be recycled.

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Key Words

Reduction of Imines, Organocatalysis, Trichlorosilane

ID: J42-Y2007-0540