Synfacts 2006(12): 1243-1243  
DOI: 10.1055/s-2006-955632
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cu(I)-Catalyzed Enantioselective Hydrosilylation of Aromatic Ketones

Contributor(s): Mark Lautens, Andrew Martins
J. T. Issenhuth, S. Dagorne*, S. Bellemin-Laponnaz*
Université Louis Pasteur, Strasbourg, France
Further Information

Publication History

Publication Date:
22 November 2006 (online)

Significance

In the presence of a Cu(I)/BINAP catalyst and hydrosilane, various ketones were enantioselectively converted into the corresponding silyl ether, which upon hydrolysis afforded chiral secondary alcohols. The reaction generally gives high yields and ee values, but is limited to aromatic ketones. Kinetic experiments determined that the reaction is first-order in catalyst, silane and ketone, offering some insight into the true active catalyst.