Diastereo- and Enantioselective Conjugate Addition of α-Ketoesters to Nitroalkenes Catalyzed by a Chiral Ni(OAc)2 Complex under Mild Conditions

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• 作者：Ayako Nakamura ; Sylvain Lectard ; Daisuke Hashizume ; Yoshitaka Hamashima ; Mikiko Sodeoka
• 刊名：Journal of the American Chemical Society
• 出版年：2010
• 出版时间：March 31, 2010
• 年：2010
• 卷：132
• 期：12
• 页码：4036-4037
• 全文大小：199K
• 年卷期：v.132,no.12(March 31, 2010)
• ISSN：1520-5126

文摘

A highly efficient, catalytic, diastereo- and enantioselective conjugate addition of α-ketoesters to nitroalkenes has been devised. The reaction was applicable to various substrates. Notably, the combination of endogenous and exogenous bases was effective, allowing a small amount of the catalyst (0.1−1 mol % Ni) to promote the reaction efficiently. The synthetic utility of this reaction was demonstrated in the synthesis of substituted pyrrolidine derivatives, whose stereochemistry is closely related to biologically important natural products such as kainic acid.