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Acta Chimica Sinica ›› 2007, Vol. 65 ›› Issue (16): 1631-1637. Previous Articles     Next Articles

Original Articles

L-丙氨酰Betti碱催化环己酮对硝基烯不对称Michael加成反应

焦崇峻, 沈宗旋, 吴国峰, 朱金龙, 张雅文*   

  1. (苏州大学化学化工学院 江苏省有机合成重点实验室 苏州 215123)
  • 投稿日期:2007-03-30 修回日期:2007-06-01 发布日期:2007-08-28
  • 通讯作者: 张雅文

L-Alaninylated Betti Bases as Catalysts for the Asymmetric Michael Addition Reaction of Cyclohexanone to Nitroolefins

JIAO Chong-Jun; SHEN Zong-Xuan; WU Guo-Feng; ZHU Jin-Long; ZHANG Ya-Wen*   

  1. (Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry & Chemical Engineering, Suzhou University, Suzhou 215123)
  • Received:2007-03-30 Revised:2007-06-01 Published:2007-08-28
  • Contact: ZHANG Ya-Wen

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Three N-L-alaninylated Betti bases have been designed and conveniently synthesized and evaluated as organocatalysts for the asymmetric Michael addition of cyclohexanone to nitroolefins. Among them, 1a was found to be the most effective and high enantioselectivity up to ＞99% ee and excellent diastereoselectivity up to ＞99∶1 dr have been achieved. The influences of the structure and the loading of the catalyst, the amount of the additive, and the structure of the substrate have also been examined.

Key words: Michael addition, asymmetric, Betti base, nitroolefin