Rational catalyst design for the enantioselective organocatalytic hydrosilylation of aromatic ketimines

ORGN 116

Andrei V. Malkov, amalkov@chem.gla.ac.uk, Sigitas Stoncius, sigis@chem.gla.ac.uk, and Pavel Kocovsky, P.Kocovsky@chem.gla.ac.uk. Department of Chemistry, University of Glasgow, Glasgow, G12 8QQ, United Kingdom
Further improvement of a practical, organocatalytic protocol for the enantioselective reduction of prochiral N-aryl ketimines has been achieved by rational optimization of the catalyst structure. The method relies on the use of trichlorosilane as the stoichiometric reducing reagent activated by catalytic quantities of valine-derived N-methyl formamides. This metal-free protocol approaches the efficiency of the traditional, metal-catalyzed methodology, furnishing the corresponding amines in up to 96% ee at just 1 mol % catalyst loading.
 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006