Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction

doi:10.6023/cjoc201807008

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (2): 443-448.DOI: 10.6023/cjoc201807008 Previous Articles Next Articles

ARTICLE

手性咪唑氨基醇的合成及其在铜催化不对称Henry反应中的应用

毛璞^a, 杨亮茹^a, 肖咏梅^a, 袁金伟^a, 买文鹏^b, 高杰^a, 张心持^a

a 河南工业大学化学化工与环境学院河南省天然药物化学院士工作站郑州 450001;
b 河南工程学院材料工程学院郑州 451191

收稿日期:2018-07-04 修回日期:2018-08-31 发布日期:2018-09-26
通讯作者: 毛璞, 杨亮茹 E-mail:lryang@haut.edu.cn;maopu@haut.edu.cn
基金资助:
国家自然科学基金（No.21172055）、河南省教育厅自然科学基金（No.18A150004）、郑州市科技创新团队（No.131PCXTD605）和河南省高校基础研究和河南工业大学（No.2017RCJH08）资助项目.

Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction

Mao Pu^a, Yang Liangru^a, Xiao Yongmei^a, Yuan Jinwei^a, Mai Wenpeng^b, Gao Jie^a, Zhang Xinchi^a

a Academician Workstation for Natural Medicinal Chemistry of Henan Province, School of Chemical Engineering and Environment, Henan University of Technology, Zhengzhou 450001;
b School of Material and Chemical Engineering, Henan University of Engineering, Zhengzhou 451191

Received:2018-07-04 Revised:2018-08-31 Published:2018-09-26
Contact: 10.6023/cjoc201807008 E-mail:lryang@haut.edu.cn;maopu@haut.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21172055), the Natural Science Foundation of Henan Province Department of Education (No. 18A150004), the Program for Innovative Research Team from Zhengzhou City (No. 131PCXTD605), and the Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology (No. 2017RCJH08).

1. Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction.PDF(5030KB)

Abstract

Using L-phenylalaninol as chiral precursor, a series of multi-aryl substituted imidazole amino alcohol derivatives containing appended chiral functionalities were synthesized through a "four component-one pot procedure" from the condensation reaction of L-phenylalaninol, dibenzoyl (benzil), ammonium acetate and different heterocyclic aryl-aldehyde. X-ray crystal analysis confirmed that the chiral carbon retained the S configuration of L-phenylalaninol. The chiral ligands in combination with Cu(OAc)₂·H₂O catalyzed the enantioselective Henry reaction of nitromethane and aromatic aldehydes with moderate to high yields and excellent enantioselectivities (>99%) with S configuration. The easy availability of catalyst components, mild reaction conditions and high enantioselectivity make the system attractive for practical application.

Key words: chiral, imidazole amino alcohol, asymmetric Henry reaction

Cite this article

Mao Pu, Yang Liangru, Xiao Yongmei, Yuan Jinwei, Mai Wenpeng, Gao Jie, Zhang Xinchi. Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction[J]. Chin. J. Org. Chem., 2019, 39(2): 443-448.

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手性咪唑氨基醇的合成及其在铜催化不对称Henry反应中的应用

Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction

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