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Synfacts 2006(3): 0254-0254  
DOI: 10.1055/s-2006-931950
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Michael Addition of Anilines to α,β-Unsaturated N-Imides

Contributor(s): Mark Lautens, Andrew Martins
P. H. Phua, J. G. de Vries, K. K. (M.) Hii*
Imperial College London, UK and DSM Research-Life Sciences, Geleen, The Netherlands
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

In recent years, there have been many reports detailing efficient and effective asymmetric Michael reactions. Using a Pd(II)/BINAP catalyst system, a variety of two-point binding α,β-unsaturated N-imides undergo enantioselective Michael addition with a variety of anilines. Enantioselectivity is rather insensitive to electronic effects on the β-carbonyl group. It was also found that electroneutral anilines afforded the highest enantioselectivity, with highly electron-rich or -poor anilines showing erosion of stereoselectivity.