Citation: 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 shu

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

College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450000

Corresponding author: Huang Lihua, huanglh2207@163.com Wang Mincan, wangmincan@zzu.edu.cn
Received Date: 19 June 2017
Revised Date: 15 July 2017
Available Online: 9 January 2017
Fund Project: the Education Department of Henan Province 18B150028the Education Department of Henan Province 17B150014Project supported by the National Natural Science Foundation of China (No. 21272216) and the Education Department of Henan Province (Nos. 17B150014, 18B150028)the National Natural Science Foundation of China 21272216

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.
- enantioselective catalysis,
- Friedel-Crafts alkylation,
- zinc,
- semi-azacrown ether ligand
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