Asymmetric Transfer Hydrogenation of 3-(Trifluoromethyl)quinolines

被引：14
|
作者：
Guo, Ran-Ning [1 ,2 ]
Chen, Zhang-Pei [2 ]
Cai, Xian-Feng [2 ]
Zhou, Yong-Gui [2 ]
机构：
[1] Dalian Univ Technol, Dept Chem, Dalian 116012, Peoples R China
[2] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2014年 / 46卷 / 20期
基金：
美国国家科学基金会;
关键词：
chiral phosphoric acid; transfer hydrogenation; quinolines; trifluoromethyl group; ENANTIOSELECTIVE TRANSFER HYDROGENATION; CATALYZED TRANSFER HYDROGENATION; CHIRAL PHOSPHORIC-ACIDS; ALPHA-IMINO ESTERS; ORGANOCATALYTIC TRANSFER HYDROGENATION; BRONSTED ACID; HANTZSCH ESTERS; HETEROAROMATIC-COMPOUNDS; REDUCTIVE AMINATION; PERFLUOROALKYLATION REACTIONS;
D O I：
10.1055/s-0033-1338661
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A chiral phosphoric acid-catalyzed asymmetric transfer hydrogenation of 3-(trifluoromethyl) quinolines was successfully developed with up to 98% ee. The new method provides a direct and facile access to chiral 2,3-disubstituted 1,2,3,4-tetrahydroquinoline derivatives containing a stereogenic trifluoromethyl group.
引用
收藏
页码：2751 / 2756
页数：6
相关论文
共 50 条
  • [21] Synthesis of polymer/CNTs composites for the heterogeneous asymmetric hydrogenation of quinolines
    Tao, Lin
    Li, Chunzhi
    Ren, Yiqi
    Li, He
    Chen, Jian
    Yang, Qihua
    CHINESE JOURNAL OF CATALYSIS, 2019, 40 (10) : 1548 - 1556
  • [22] Synthesis of tunable bisphosphine ligands and their application in asymmetric hydrogenation of quinolines
    Wang, Xiao-Bing
    Zhou, Yong-Gui
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14): : 5640 - 5642
  • [23] Organocatalytic Approach for Transfer Hydrogenation of Quinolines, Benzoxazines and Benzothiazines
    Xiang Qiao
    Zongbi Bao
    Huabin Xing
    Yiwen Yang
    Qilong Ren
    Zhiguo Zhang
    Catalysis Letters, 2017, 147 : 1673 - 1678
  • [24] Organocatalytic Approach for Transfer Hydrogenation of Quinolines, Benzoxazines and Benzothiazines
    Qiao, Xiang
    Bao, Zongbi
    Xing, Huabin
    Yang, Yiwen
    Ren, Qilong
    Zhang, Zhiguo
    CATALYSIS LETTERS, 2017, 147 (07) : 1673 - 1678
  • [25] A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
    Sheng, Jie
    Fan, Congbin
    Wu, Jie
    CHEMICAL COMMUNICATIONS, 2014, 50 (41) : 5494 - 5496
  • [26] Facile construction of three contiguous stereogenic centers via dynamic kinetic resolution in asymmetric transfer hydrogenation of quinolines
    Chen, Mu-Wang
    Cai, Xian-Feng
    Chen, Zhang-Pei
    Shi, Lei
    Zhou, Yong-Gui
    CHEMICAL COMMUNICATIONS, 2014, 50 (83) : 12526 - 12529
  • [27] Asymmetric transfer hydrogenation of imines
    Uematsu, N
    Fujii, A
    Hashiguchi, S
    Ikariya, T
    Noyori, R
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (20) : 4916 - 4917
  • [28] Kinetic Resolution of Axially Chiral 5-or 8-Substituted Quinolines via Asymmetric Transfer Hydrogenation
    Wang, Jie
    Chen, Mu-Wang
    Ji, Yue
    Hu, Shu-Bo
    Zhou, Yong-Gui
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (33) : 10413 - 10416
  • [29] Asymmetric Transfer Hydrogenation of Cyclobutenediones
    Lan, Shouang
    Huang, Huangjiang
    Liu, Wenjun
    Xu, Chao
    Lei, Xiang
    Dong, Wennan
    Liu, Jinggong
    Yang, Shuang
    Cotman, Andrej Emanuel
    Zhang, Qi
    Fang, Xinqiang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (07) : 4942 - 4957
  • [30] Asymmetric Transfer Hydrogenation in Water
    Tang Yuanfu
    Deng Jingen
    PROGRESS IN CHEMISTRY, 2010, 22 (07) : 1242 - 1253
12345