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Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 1: 237 - 245

DOI: https://doi.org/10.6023/cjoc201706027

Articles

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

  • Hua Yuanzhao ,
  • Han Xingwang ,
  • Huang Lihua ,
  • Wang Mincan
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  • College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450000

Received date: 2017-06-19

  Revised date: 2017-07-15

  Online published: 2017-08-09

Supported by

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

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Abstract

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

Cite this article

Hua Yuanzhao , Han Xingwang , Huang Lihua , Wang Mincan . Asymmetric Friedel-Crafts Alkylation of Pyrrole with Chalcones Catalyzed by a Dinuclear Zinc Catalyst[J]. Chinese Journal of Organic Chemistry, 2018 , 38(1) : 237 -245 . DOI: 10.6023/cjoc201706027

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