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（英文）  

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

作　　者：毛璞 杨亮茹 肖咏梅 袁金伟 买文鹏[2] 高杰 张心持 Mao Pu;Yang Liangru;Xiao Yongmei;Yuan Jinwei;Mai Wenpeng;Gao Jie;Zhang Xinchi(Academician Workstation for Natural Medicinal Chemistry of Henan Province, School of Chemical Engineering and Environment, Henan University of Technology, Zhengzhou 450001;School of Material and Chemical Engineering, Henan University of Engineering, Zhengzhou 451191)

机构地区：[1]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 [2]河南工程学院材料工程学院,郑州451191

出　　处：《有机化学》2019年第2期443-448,共6页Chinese Journal of Organic Chemistry

基　　金：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);the Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology(No.2017RCJH08)~~

摘　　要：以L-苯丙氨醇、连苯甲酰、醋酸铵及不同的杂芳醛为原料,经"四组分一锅煮"缩合反应合成了系列多芳基取代的手性咪唑氨基醇衍生物.X射线单晶衍射测定证明,在缩合反应中,L-苯丙氨醇的构型保持.将手性配体与Cu(OAc)2·H2O用于催化硝基甲烷与芳醛的不对称Henry反应,可以中等或高收率,高对映选择性(>99%)获得S构型的产物.此体系催化剂合成简单、反应条件温和、对映选择性高,有很好的应用前景.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.

关 键 词：手性 咪唑氨基醇 不对称HENRY反应 

分 类 号：O621.251[理学—有机化学]