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
  • [21] Enantioselective synthesis of 1-arylethanediols by rhodium-catalyzed transfer hydrogenation of α-tosyloxyarylketones
    Lee, Do-Min
    Kumaraswamy, Gullapalli
    Lee, Kee-In
    MONATSHEFTE FUR CHEMIE, 2009, 140 (01): : 73 - 78
  • [22] Phosphoric Acid-Catalyzed Enantioselective Transfer Hydrogenation of N-Aryl-ortho-Hydroxybenzophenone Ketimines
    Thanh Binh Nguyen
    Bousserouel, Hadjira
    Wang, Qian
    Gueritte, Francoise
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) : 257 - 262
  • [23] Enantioselective Transfer Hydrogenation of α-Methoxyimino-β-keto Esters
    Tharra, Prabhakara R.
    Svejkar, Jiri
    Jadhav, Abhijeet S.
    Necas, Marek
    Dub, Pavel A.
    Halls, Mathew D.
    Svenda, Jakub
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18) : 12902 - 12911
  • [24] Enantioselective Organocatalytic Transfer Hydrogenation of 1,2-Dihydroquinoline through Formation of Aza-o-xylylene
    Li, Guangxun
    Liu, Hongxin
    Lv, Gang
    Wang, Yingwei
    Fu, Qingquan
    Tang, Zhuo
    ORGANIC LETTERS, 2015, 17 (17) : 4125 - 4127
  • [25] Highly enantioselective synthesis of anti aryl β-hydroxy α-amino esters via DKR transfer hydrogenation
    Liu, Zhuqing
    Shultz, C. Scott
    Sherwood, Candice A.
    Krska, Shane
    Dormer, Peter G.
    Desmond, Richard
    Lee, Claire
    Sherer, Edward C.
    Shpungin, Joseph
    Cuff, James
    Xu, Feng
    TETRAHEDRON LETTERS, 2011, 52 (14) : 1685 - 1688
  • [26] Enantioselective Synthesis of Quinolizidines and Indolizidines via a Catalytic Asymmetric Hydrogenation Cascade
    Rueping, Magnus
    Hubener, Lukas
    SYNLETT, 2011, (09) : 1243 - 1246
  • [27] Highly enantioselective synthesis of cyclic sulfamidates and sulfamides via rhodium-catalyzed transfer hydrogenation
    Lee, Sun Ah
    Kwak, Se Hun
    Lee, Kee-In
    CHEMICAL COMMUNICATIONS, 2011, 47 (08) : 2372 - 2374
  • [28] Chiral-at-metal iridium complex for efficient enantioselective transfer hydrogenation of ketones
    Tian, Cheng
    Gong, Lei
    Meggers, Eric
    CHEMICAL COMMUNICATIONS, 2016, 52 (22) : 4207 - 4210
  • [29] Enantioselective Total Synthesis of (+)-Lysergol: A Formal anti-Carbopalladation/Heck Cascade as the Key Step
    Milde, Bastian
    Pawliczek, Martin
    Jones, Peter G.
    Werz, Daniel B.
    ORGANIC LETTERS, 2017, 19 (07) : 1914 - 1917
  • [30] Highly Enantioselective Synthesis of Sultams via Pd-Catalyzed Hydrogenation
    Yu, Chang-Bin
    Wang, Da-Wei
    Zhou, Yong-Gui
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) : 5633 - 5635