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Proc Natl Acad Sci U S A. 2005 Mar 8;102(10):3570-5. Epub 2005 Feb 22.

A remarkably effective copper(II)-dipyridylphosphine catalyst system for the asymmetric hydrosilylation of ketones in air.

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  • 1Open Laboratory of Chirotechnology, Institute of Molecular Technology for Drug Discovery and Synthesis, Hong Kong Polytechnic University, Kowloon, Hong Kong.

Abstract

The combination of catalytic amounts of optically active dipyridylphosphine and CuF(2) along with hydride donor PhSiH(3) generated in situ a remarkably reactive catalyst system (substrate-to-ligand molar ratio up to 100,000) for the highly enantioselective hydrosilylation of a broad spectrum of aryl alkyl ketones (up to 97% enantiomeric excess) in normal atmosphere and at mild conditions (ambient temperature to -20 degrees C, compatible with traces of moisture) in the absence of base additives. Furthermore, a highly effective catalytic asymmetric hydrosilylation of unsymmetrical diarylketones using this catalyst system was also realized (up to 98% enantiomeric excess). The introduction of the dipyridylphosphine ligands in the air-accelerated and inexpensive metal-mediated asymmetric hydrosilylation of ketones makes the present system highly attractive and thus provides an excellent opportunity for practical applications.

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