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Synfacts 2010(12): 1377-1377  
DOI: 10.1055/s-0030-1258905
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Asymmetric Michael Addition to 4-Oxo-4-arylbutenoates

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
Z. Wang, D. Chen, Z. Yang, S. Bai, X. Liu, L. Lin, X. Feng*
Sichuan University, Chengdu, P. R. of China
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Publication History

Publication Date:
22 November 2010 (online)

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Significance

In this paper, the authors report a catalytic asymmetric protocol for the Michael ­addition of 1,3-dicarbonyl compounds and nitro­methane to (E)-4-oxo-4-arylbutenoates mediated by the chiral N,N′-dioxide-Sc(OTf)3 system. A wide range of products is obtained with high yields (up to 97%) and excellent enantioselectivities (up to >99% ee). The procedure is notable for mild conditions and operational simplicity, and can be accomplished on a gram scale. Addition of dicarbonyl compounds demonstrated a small positive non-linear effect, implying the presence of a dimeric species in the catalytic system. A transition state rationalizing the asymmetric induction has been proposed.