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化学学报
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化学学报 ›› 2007, Vol. 65 ›› Issue (16): 1631-1637. 上一篇    下一篇

研究论文

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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合成了3个手性Betti碱的L-丙氨酰衍生物, 并用它们来催化环己酮与硝基烯的Michael加成反应. 发现1a是其中最有效的催化剂, ee值最高大于99%, dr值最高大于99∶1. 考察了催化剂结构与用量、添加剂用量、底物结构等因素对反应的化学产率和光学收率的影响.

关键词: Michael加成反应, 不对称, Betti碱, 硝基烯

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