Citation: 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]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 443-448. doi: 10.6023/cjoc201807008 shu

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

Corresponding author: Mao Pu, maopu@haut.edu.cn Yang Liangru, lryang@haut.edu.cn
Received Date: 4 July 2018
Revised Date: 31 August 2018
Available Online: 26 February 2018
Fund Project: the Program for Innovative Research Team from Zhengzhou City 131PCXTD605the National Natural Science Foundation of China 21172055the Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology 2017RCJH08Project 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)the Natural Science Foundation of Henan Province Department of Education 18A150004

Figures(3)

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.
- chiral,
- imidazole amino alcohol,
- asymmetric Henry reaction
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