Chinese Journal of Organic Chemistry >
Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction
Received date: 2018-07-04
Revised date: 2018-08-31
Online published: 2018-09-26
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).
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
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
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