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Synfacts 2007(3): 0280-0280  
DOI: 10.1055/s-2007-968240
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Conjugate Addition Catalyzed by Chiral Lithium Amides

Contributor(s): Hisashi Yamamoto, Joshua P. Abell
N. Duguet, A. Harrison-Marchand, J. Maddaluno*, K. Tomioka*
Université et INSA de Rouen, France and Kyoto University, Kyoto, Japan
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

While the stereoselective conjugate addition of various nucleophiles to α,β-unsaturated substrates has been utilized for a large number of chiral catalyzed systems, the use of lithium enolates derived from ketones or esters has been sparsely demonstrated. The authors describe the addition of unstabilized lithium enolates to a α,β-unsaturated ester in high yield and moderate enantio­selectivity.