Ruthenium-Catalyzed Hydrogenation of Carbocyclic Aromatic Amines: Access to Chiral Exocyclic Amines

被引：27
|
作者：
Yan, Zhong [1 ,2 ]
Xie, Huan-Ping [1 ]
Shen, Hong-Qiang [1 ]
Zhou, Yong-Gui [1 ,3 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 04期
基金：
中国国家自然科学基金;
关键词：
ASYMMETRIC TRANSFER HYDROGENATION; N-HETEROAROMATIC COMPOUNDS; DIASTEREOSELECTIVE HYDROGENATION; ENANTIOSELECTIVE HYDROGENATION; ARENE HYDROGENATION; HETEROGENEOUS CATALYSTS; SUBSTITUTED QUINOLINES; KINETIC RESOLUTION; DERIVATIVES; SALTS;
D O I：
10.1021/acs.orglett.7b04060
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first highly enantioselective hydrogenation of carbocyclic aromatic amines has been successfully realized using in situ-generated chiral ruthenium complex as catalyst, affording facile access to chiral exocyclic amines with up to 98% ee.
引用
收藏
页码：1094 / 1097
页数：4
相关论文
共 50 条
  • [1] RUTHENIUM-CATALYZED HYDROGENATION OF AROMATIC AMINES PROMOTED BY LITHIUM HYDROXIDE
    NISHIMURA, S
    KONO, Y
    OTSUKI, Y
    FUKAYA, Y
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1971, 44 (01) : 240 - +
  • [2] A general ruthenium-catalyzed synthesis of aromatic Amines
    Hollmann, Dirk
    Baehn, Sebastian
    Tillack, Annegret
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (43) : 8291 - 8294
  • [3] Synthesis of Chiral Exocyclic Amines by Asymmetric Hydrogenation of Aromatic Quinolin-3-amines
    Cai, Xian-Feng
    Guo, Ran-Ning
    Chen, Mu-Wang
    Shi, Lei
    Zhou, Yong-Gui
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (24) : 7245 - 7248
  • [4] Towards a general ruthenium-catalyzed hydrogenation of secondary and tertiary amides to amines
    Cabrero-Antonino, Jose R.
    Alberico, Elisabetta
    Junge, Kathrin
    Junge, Henrik
    Beller, Matthias
    [J]. CHEMICAL SCIENCE, 2016, 7 (05) : 3432 - 3442
  • [5] RUTHENIUM-CATALYZED CARBONYLATION OF CYCLIC AMINES
    JENNER, G
    BITSI, G
    SCHLEIFFER, E
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1987, 39 (02): : 233 - 236
  • [6] Ruthenium-Catalyzed Aerobic Oxidation of Amines
    Ray, Ritwika
    Hazari, Arijit Singha
    Lahiri, Goutam Kumar
    Maiti, Debabrata
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) : 2138 - 2148
  • [7] Dehydrogenation of aromatic amines to imines via ruthenium-catalyzed hydrogen transfer
    Éll, AH
    Samec, JSM
    Brasse, C
    Bäckvall, JE
    [J]. CHEMICAL COMMUNICATIONS, 2002, (10) : 1144 - 1145
  • [8] Ruthenium-Catalyzed Selective α,β-Deuteration of Bioactive Amines
    Neubert, Lorenz
    Michalik, Dirk
    Baehn, Sebastian
    Imm, Sebastian
    Neumann, Helfried
    Atzrodt, Jens
    Derdau, Volker
    Holla, Wolfgang
    Beller, Matthias
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (29) : 12239 - 12244
  • [9] Chiral ruthenium-catalyzed hydrogenation of β-keto sulfoxides
    De Paule, SD
    Piombo, L
    Ratovelomanana-Vidal, V
    Greck, C
    Genêt, JP
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (08) : 1535 - 1537
  • [10] Ruthenium-catalyzed deaminative redistribution of primary and secondary amines
    Kostera, S.
    Wyrzykiewicz, B.
    Pawluc, P.
    Marciniec, B.
    [J]. DALTON TRANSACTIONS, 2017, 46 (35) : 11552 - 11555
12345