有机化学 ›› 2015, Vol. 35 ›› Issue (10): 2119-2124.DOI: 10.6023/cjoc201505013 上一篇    下一篇

研究论文

芳甲叉双噁唑啉-铜络合物催化三氟甲基丙酮酸酯与吲哚的傅-克烷基化反应研究

殷伯翰, 吴燕华, 麻红利, 马晓东, 傅滨, 刘吉平   

  1. 中国农业大学理学院 北京 100193
  • 收稿日期:2015-05-07 修回日期:2015-06-08 发布日期:2015-06-16
  • 通讯作者: 傅滨, 刘吉平 E-mail:fubinchem@cau.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. J1210064, 21172255)资助项目.

Studies on the Asymmetric Catalytic Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by Heteroarylidene-BOX-Cu Complexes

Yin Bohan, Wu Yanhua, Ma hongli, Ma Xiaodong, Fu Bin, Liu Jiping   

  1. College of Science, China Agricultural University, Beijing 100193
  • Received:2015-05-07 Revised:2015-06-08 Published:2015-06-16
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. J1210064, 21172255).

报道了芳甲叉双噁唑啉-铜络合物催化三氟甲基丙酮酸酯对吲哚的傅-克烷基化反应, 探讨了配体结构、溶剂、温度等因素对反应的影响. 研究表明, 反应表现出高活性和中等程度以上的对映选择性, 吲哚环上取代基对催化反应有重要的影响. 提供了一种合成含手性三氟甲基季碳吲哚化合物的新方法.

关键词: 三氟甲基, 傅-克烷基化, 吲哚, 双噁唑啉

This paper reported the reaction of indoles with trifluoromethyl pyruvate catalyzed by heteroaryliden-tethered bis-oxazoline-Cu(II) complex, and the effects of ligand structure, solvent, temperature and different indole substrates on the catalytic reactions were investigated. The results indicate that the reaction furnished high reactivity and moderate to good enantioselectivity, and the substituents on the indole ring have important impact on the reaction. The reaction can afford the indole derivatives with a chiral tertiary carbon center bearing trifluoromethyl substituent in high yields with moderate to good enantioselectivities.

Key words: trifluoromethyl, Friedel-Crafts, indole, bis-oxazoline