有机化学 ›› 2013, Vol. 33 ›› Issue (07): 1483-1489.DOI: 10.6023/cjoc201301001 上一篇    下一篇

研究论文

高选择性相转移催化原位产生不饱和亚胺参与的不对称Michael反应

陈金全, 康泰然, 刘敬林, 何龙, 刘全忠   

  1. 西华师范大学化学化工学院化学合成与污染控制四川省重点实验室 南充 637009
  • 收稿日期:2013-01-01 修回日期:2013-02-20 发布日期:2013-03-06
  • 通讯作者: 刘全忠 E-mail:quanzhongliu@cwnu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 20772097, 21102116)资助项目.

Phase Transfer Catalyzed Enantioselective and Diastereoselective Conjugate Additions of Glycinate Imine to Unsaturated Imines Formed in situ from Sulfonylindoles

Chen Jinquan, Kang Tairan, Liu Jinglin, He Long, Liu Quanzhong   

  1. Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637009
  • Received:2013-01-01 Revised:2013-02-20 Published:2013-03-06
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21102116, 20772097).

在相转移催化条件下, 二苯甲酮亚胺甘氨酸叔丁酯与原位生成的α,β-不饱和亚胺发生共轭加成反应, 以最高99%的产率, 95%的对映选择性以及5:1的非对映选择性得到相应顺式异构体为主的β-取代色氨酸衍生物.

关键词: 相转移催化, 二苯甲酮亚胺甘氨酸叔丁酯, α,β-不饱和亚胺, β-取代色氨酸衍生物

Enantio-and diastereo-selective conjugate addition of glycine derivatives to α,β-unsaturated imines generated in situ from sulfonylindoles under phase transfer catalysis was described. The corresponding syn β-substituted tryptophan derivatives were obtained in up to 99% yield with up to 95% ee and 5:1 dr.

Key words: phase transfer catalysis, glycine derivative, sulfonylindoles, β-substituted tryptophans