Synthesis of chiral sultams via palladiu-mcatalyzed intramolecular asymmetric reductive amination

被引:43
|
作者
Song, Bo [1 ,2 ]
Yu, Chang-Bin [1 ]
Ji, Yue [1 ]
Chen, Mu-Wang [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] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
BORROWING HYDROGEN METHODOLOGY; PD-CATALYZED HYDROGENATION; EXCESS N-BUTYLLITHIUM; CYCLIC KETIMINES; ENANTIOSELECTIVE SYNTHESIS; COOPERATIVE CATALYSIS; SULFONYL KETIMINES; PHOSPHORIC-ACID; ALCOHOLS; RUTHENIUM;
D O I
10.1039/c6cc09493g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel palladium-catalyzed intramolecular reductive amination of ketones with weakly nucleophilic sulfonamides has been developed in the presence of a Bronsted acid, giving a wide range of chiral gamma-, delta-, and epsilon-sultams in high yields and up to 99% of enantioselectivity.
引用
收藏
页码:1704 / 1707
页数:4
相关论文
共 50 条
  • [1] Synthesis of chiral γ-sultams through intramolecular reductive amination with sulfonylcarbamate as N-source
    Song, Bo
    Ji, Yue
    Hu, Shu-Bo
    Yu, Chang-Bin
    Zhou, Yong-Gui
    TETRAHEDRON LETTERS, 2017, 58 (15) : 1528 - 1530
  • [2] Enantioselective synthesis of tetrahydroisoquinolines via catalytic intramolecular asymmetric reductive amination
    Liu, Ruixia
    Han, Jingkuo
    Li, Bin
    Liu, Xian
    Wei, Zhao
    Wang, Jiaxin
    Wang, Qiaofeng
    Jiang, Ru
    Nie, Huifang
    Zhang, Shengyong
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (09) : 1930 - 1934
  • [4] Direct Asymmetric Reductive Amination for the Synthesis of Chiral -Arylamines
    Huang, Haizhou
    Liu, Xiaoyan
    Zhou, Le
    Chang, Mingxin
    Zhang, Xumu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (17) : 5309 - 5312
  • [5] Enantioselective Synthesis of β-Arylamines via Chiral Phosphoric Acid-Catalyzed Asymmetric Reductive Amination
    Kim, Kyung-Hee
    Lee, Chun-Young
    Cheon, Cheol-Hong
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (12): : 6367 - 6374
  • [6] Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines
    Yang, Tao
    Guo, Xiaochong
    Yin, Qin
    Zhang, Xumu
    CHEMICAL SCIENCE, 2019, 10 (08) : 2473 - 2477
  • [7] Dynamic Kinetic Asymmetric Reductive Amination: Synthesis of Chiral Primary β-Amino Lactams
    Lou, Yazhou
    Hu, Yutao
    Lu, Jiaxiang
    Guan, Fanfu
    Gong, Gelin
    Yin, Qin
    Zhang, Xumu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (43) : 14193 - 14197
  • [8] Synthesis of Chiral Trifluoromethyl-Substituted Hydrazines via Pd-Catalyzed Asymmetric Hydrogenation and Reductive Amination
    Chen, Zhang-Pei
    Hu, Shu-Bo
    Zhou, Ji
    Zhou, Yong-Gui
    ACS CATALYSIS, 2015, 5 (10): : 6086 - 6089
  • [9] Synthesis of azabicycles using intramolecular reductive amination
    Lanier, Emily
    Wolfe, Amanda
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [10] Enantioselective Direct Synthesis of Free Cyclic Amines via Intramolecular Reductive Amination
    Zhang, Ying
    Yan, Qiaozhi
    Zi, Guofu
    Hou, Guohua
    ORGANIC LETTERS, 2017, 19 (16) : 4215 - 4218