Enantioselective transfer hydrogenation, a key step for the synthesis of 3-aminotetrahydroquinolines

被引:10
|
作者
Aillerie, Alexandre [1 ]
de Talence, Vincent Lemau [1 ]
Dumont, Clement [1 ]
Pellegrini, Sylvain [1 ]
Capet, Frederic [1 ]
Bousquet, Till [1 ]
Pelinski, Lydie [1 ]
机构
[1] Univ Artois, Univ Lille, CNRS, UMR 8181,Cent Lille,ENSCL,UCCS, F-59000 Lille, France
关键词
ASYMMETRIC TRANSFER HYDROGENATION; ORGANOCATALYTIC TRANSFER HYDROGENATION; CYANOBACTERIUM ANABAENA-CYLINDRICA; CHIRAL PHOSPHORIC-ACIDS; BRONSTED ACID; QUINOLINES; ANACHELIN; CYCLIZATION; REDUCTION; TETRAHYDROQUINOLINES;
D O I
10.1039/c6nj02249a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An enantioselective transfer hydrogenation has been successfully achieved to furnish 3-aminotetrahydroquinolines. The reaction was conducted in the presence of Hantzsch dihydropyridine and a catalytic amount of chiral phosphoric acid under mild conditions.
引用
收藏
页码:9034 / 9037
页数:4
相关论文
共 50 条
  • [41] Highly Enantioselective SPINOL-Derived Phosphoric Acid Catalyzed Transfer Hydrogenation of Diverse C=N-Containing Heterocycles
    Zhang, Yiliang
    Zhao, Rong
    Bao, Robert Li-Yuan
    Shi, Lei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (15) : 3344 - 3351
  • [42] Step-Economical Synthesis of Tetrahydroquinolines by Asymmetric Relay Catalytic Friedlander Condensation/Transfer Hydrogenation
    Ren, Lei
    Lei, Tao
    Ye, Jia-Xi
    Gong, Liu-Zhu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (03) : 771 - 774
  • [43] Enantioselective Hydrogenation and Transfer Hydrogenation of Bulky Ketones Catalysed by a Ruthenium Complex of a Chiral Tridentate Ligand
    Diaz-Valenzuela, M. Belen
    Phillips, Scott D.
    France, Marcia B.
    Gunn, Mary E.
    Clarke, Matthew L.
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (05) : 1227 - 1232
  • [44] Direct enantioselective access to 4-substituted tetrahydroquinolines by catalytic asymmetric transfer hydrogenation of quinolines
    Rueping, Magnus
    Theissmann, Thomas
    Stoeckel, Mirjam
    Antonchick, Andrey P.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (19) : 6844 - 6850
  • [45] Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones through Organocatalytic Transfer Hydrogenation of 2-Hydroxypyrimidines
    Meng, Fan-Jie
    Shi, Lei
    Feng, Guang-Shou
    Sun, Lei
    Zhou, Yong-Gui
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (07) : 4435 - 4442
  • [46] Enantioselective Iridium-Catalyzed Hydrogenation of 3,4-Disubstituted Isoquinolines
    Shi, Lei
    Ye, Zhi-Shi
    Cao, Liang-Liang
    Guo, Ran-Ning
    Hu, Yue
    Zhou, Yong-Gui
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (33) : 8286 - 8289
  • [47] Transfer Hydrogenation in Water: Enantioselective, Catalytic Reduction of (E)-β,β-Disubstituted Nitroalkenes
    Soltani, Omid
    Ariger, Martin A.
    Carreira, Erick M.
    ORGANIC LETTERS, 2009, 11 (18) : 4196 - 4198
  • [48] Enantioselective Organocatalytic Partial Transfer Hydrogenation of Lactone-Fused Quinolines
    Aillerie, Alexandre
    de Talance, Vincent Lemau
    Moncomble, Aurelien
    Bousquet, Till
    Pelinski, Lydie
    ORGANIC LETTERS, 2014, 16 (11) : 2982 - 2985
  • [49] Highly Enantioselective Rh-catalyzed Transfer Hydrogenation of α-Functionalized Arylketones
    Lee, Do-Min
    Kwak, Se Hun
    Lee, Kee-In
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2009, 30 (06) : 1317 - 1324
  • [50] A highly enantioselective bronsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids
    Rueping, Magnus
    Antonchick, Andrey R.
    Theissmann, Thomas
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (22) : 3683 - 3686