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Synfacts 2006(5): 0512-0512  
DOI: 10.1055/s-2006-934455
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Direct Asymmetric Vinylogous Michael Reaction

Contributor(s): Benjamin List, Subhas Chandra Pan
J-W. Xie, L. Yue, D. Xue, X-L. Ma, Y-C. Chen, Y. Wu, J. Zhu, J-G. Deng*
Sichuan University, Chengdu; Chengdu Institute of Organic Chemistry; Graduate School of Chinese Academy of Sciences, Beijing, P. R. of China
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Publication History

Publication Date:
21 April 2006 (online)

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Significance

The authors report an asymmetric direct vinylogous Michael addition of α,α-dicyano­olefins to α,β-unsaturated aldehydes. Commercially available α,α-diphenylprolinol (1) in combination with p-nitrobenzoic acid (PNBA) has been found to be an effective catalytic system for the reaction. With 20 mol% of catalyst 1, moderate to good yields (40-91%) and good enantioselectivities (68-98%) are obtained for a variety of α,α-dicyanoolefins.