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

doi:10.6023/cjoc201706027

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

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双锌催化剂催化的吡咯与查尔酮类化合物的不对称傅-克烷基化反应

华远照, 韩兴旺, 黄利华, 王敏灿

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 E-mail:huanglh2207@163.com;wangmincan@zzu.edu.cn
基金资助:
国家自然科学基金（No.21272216）及河南省教育厅（Nos.17B150014，18B150028）资助项目.

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

Hua Yuanzhao, Han Xingwang, Huang Lihua, Wang Mincan

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 E-mail:huanglh2207@163.com;wangmincan@zzu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272216) and the Education Department of Henan Province (Nos. 17B150014, 18B150028).

1. Asymmetric Friedel-Crafts Alkylation of Pyrrole with Chalcones Catalyzed by a Dinuclear Zinc Catalyst.PDF(1281KB)

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

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Hua Yuanzhao, Han Xingwang, Huang Lihua, Wang Mincan. Asymmetric Friedel-Crafts Alkylation of Pyrrole with Chalcones Catalyzed by a Dinuclear Zinc Catalyst[J]. Chin. J. Org. Chem., 2018, 38(1): 237-245.

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双锌催化剂催化的吡咯与查尔酮类化合物的不对称傅-克烷基化反应

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

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