有机化学 ›› 2012, Vol. 32 ›› Issue (12): 2322-2327.DOI: 10.6023/cjoc201207011 上一篇    下一篇

研究论文

二乙基锌对原位产生吲哚亚胺的对映选择性加成反应

倪承燕, 李文科, 何龙, 刘全忠, 康泰然   

  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 637000
  • 收稿日期:2012-07-07 修回日期:2012-08-02 发布日期:2012-08-06
  • 通讯作者: 刘全忠 E-mail:quanzhongliu@sohu.com
  • 基金资助:

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

Enantioselective Conjugate Addition of Diethylzinc to Vinylogous Imines Generated in situ from Sulfonyl Indoles

Ni Chengyan, Li Wenke, He Long, Liu Quanzhong, Kang Tairan   

  1. Chemical Synthesis and pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637000
  • Received:2012-07-07 Revised:2012-08-02 Published:2012-08-06
  • Supported by:

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

发展了乙基锌对原位产生的不饱和亚胺的对映选择性共轭加成, 磺酰吲哚衍生物在乙基锌存在下原位生成不饱和亚胺, 手性亚磷酰胺配体-铜络合物催化二乙基锌对该原位产生的不饱和亚胺反应以最高99%的产率和80%的对映选择性得到了一系列3位取代的光学活性的吲哚衍生物.

关键词: 对映选择性共轭加成, 磺酰吲哚衍生物, 不饱和亚胺

Enantioselective conjugate addition of diethyl zinc to vinylogous imines generated in situ from sulfonyl indoles was developed. Various sulfonyl indoles reacted with diethyl zinc in the presence of chiral phosphoramidites in combination with copper triflate affording the corresponding indole substituted alkanes in up to 99% yield with moderate to good enantioselectivity (up to 80% ee).

Key words: vinylogous imines, enantioselective conjugate addition, sulfonyl indoles