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Article

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

Supporting Info

Andrei V. Malkov,* Marek Figlus, Sigitas Ston

ius, and Pavel Ko

ovský*;

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

J. Org. Chem., 2007, 72 (4), pp 1315–1325

DOI: 10.1021/jo062215i

Publication Date (Web): January 18, 2007

†

Dedicated to Prof. Gilbert Stork on the occasion of his 85th birthday.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, amalkov@chem.gla.ac.uk, ; , pavelk@chem.gla.ac.uk

Abstract

Asymmetric reduction of ketimines 1 with trichlorosilane can be catalyzed by N-methylvaline-derived Lewis-basic formamides 3a−d with high enantioselectivity (≤95% ee) and low catalyst loading (1−5 mol %) at room temperature in toluene. Appending a fluorous tag, as in 5a−c, simplifies the isolation procedure, while preserving high enantioselectivity (≤92% ee).

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Published In Issue February 16, 2007
Received October 25, 2006

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Article

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