Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (1): 237-245.DOI: 10.6023/cjoc201706027 Previous Articles     Next Articles

Special Issue: 碳氢活化合辑2018-2019



华远照, 韩兴旺, 黄利华, 王敏灿   

  1. 郑州大学化学与分子工程学院 郑州 450000
  • 收稿日期:2017-06-19 修回日期:2017-07-15 发布日期:2017-08-09
  • 通讯作者: 黄利华, 王敏灿;
  • 基金资助:


Asymmetric Friedel-Crafts Alkylation of Pyrrole with Chalcones Catalyzed by a Dinuclear Zinc Catalyst

Hua Yuanzhao, Han Xingwang, Huang Lihua, Wang Mincan   

  1. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450000
  • Received:2017-06-19 Revised:2017-07-15 Published:2017-08-09
  • Contact: 10.6023/cjoc201706027;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272216) and the Education Department of Henan Province (Nos. 17B150014, 18B150028).

An intramolecular dinuclear zinc complex was used in asymmetric Friedel-Crafts alkylation of pyrrole with a wide range of chalcone derivatives. This dinuclear zinc complex was prepared in situ by reacting the chiral ligand (S,S)-1 with 2 equiv. of ZnEt2. A series of β-pyrrole-substituted dihydrochalcones were formed mostly in excellent yields (up to 99%) and excellent enantioselectivities (up to >99% ee) by using 15 mol% catalyst loading under mild conditions. A possible mechanism was proposed to explain the origin of the asymmetric induction.

Key words: enantioselective catalysis, Friedel-Crafts alkylation, zinc, semi-azacrown ether ligand