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Synfacts 2005(2): 0238-0238  
DOI: 10.1055/s-2005-916082
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Michael Addition of Dialkylzinc to α,β-Unsaturated Imines

Contributor(s): Mark Lautens, Y. Eric Fang
J. Esquivias, R. G. Arrayás, J. C. Carretero
Universidad Autónoma de Madrid, Spain
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Publication History

Publication Date:
25 October 2005 (online)

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Significance

Cu(I)-catalyzed conjugated addition of dialkylzinc to α,β-unsaturated (2-pyridyl)sulfonyl ketimine afforded the corresponding enamine product in good yield. Good ee was obtained in the case of dimethylzinc addition using 10 mol% CuTC and 10mol% Feringa’s monodentate phosphoramidite ligand in toluene at -20 ºC.