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Enantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea

Tomotaka Okino, Yasutaka Hoashi, Tomihiro Furukawa, Xuenong Xu and Yoshiji Takemoto*

*Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan, Email: takemotopharm.kyoto-u.ac.jp

T. Okino, Y. Hoashi, T. Fukukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc., 2005, 127, 119-125.

DOI: 10.1021/ja044370p (free Supporting Information)


Abstract

A new bifunctional catalyst bearing a thiourea moiety and an amino group was highly efficient for the asymmetric Michael reaction of 1,3-dicarbonyl compounds to nitroolefins to afford the Michael adducts with high enantio- and diastereoselectivity.

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Key Words

Michael Addition, Organocatalysis, Nitro Compounds


ID: J48-Y2005-2120