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Synfacts 2008(5): 0485-0485  
DOI: 10.1055/s-2008-1072664
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Enantioselective Hydroacylation of Ketones

Contributor(s): Mark Lautens, Praew Thansandote
Z. Shen, H. A. Khan, V. M. Dong*
University of Toronto, Canada
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Publication History

Publication Date:
23 April 2008 (online)

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Significance

A conceptually novel approach to enantioselective lactonization is presented based on a previously unknown Rh-catalyzed C-H bond activation and intramolecular hydroacylation of ketones. The phosphine ligand is crucial since increased phosphine basicities improved the selectivity of the product over the competing decarbonylation of starting material. Excellent yields and enantioselectivities are seen for a variety of aromatic and aliphatic ketones.