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Synfacts 2009(3): 0280-0280  
DOI: 10.1055/s-0028-1087746
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Synthesis of 1,4-Diketones

Contributor(s): Mark Lautens, Jacki Kitching
C. T. Avetta, Jr., L. C. Konkol, C. N. Taylor, K. C. Dugan, C. L. Stern, R. J. Thomson*
Northwestern University, Evanston, USA
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

As an extension on previous ­research concerning the formation of carbon-­carbon bonds via silyl bis-enol ethers (Org. Lett. 2007, 9, 4667), the authors now provide a general procedure for the oxidative dimerization and cross-coupling of cyclic ketones. In general, the resulting 1,4-diketones are afforded in good yield and with high diastereoselectivity. A stereochemical model based on a Thorpe-Ingold effect is provided to rationalize the observed trends.