Enantioselective C(sp3)-H Amidation of Thioamides Catalyzed by a CobaltIII/Chiral Carboxylic Acid Hybrid System

被引：197
|
作者：
Fukagawa, Seiya [1 ]
Kato, Yoshimi [1 ]
Tanaka, Ryo [1 ]
Kojima, Masahiro [1 ]
Yoshino, Tatsuhiko [1 ]
Matsunaga, Shigeki [1 ]
机构：
[1] Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 04期
关键词：
asymmetric catalysis; C-H activation; chiral carboxylic acids; cobalt; thioamide; C-H ACTIVATION; CHIRAL CYCLOPENTADIENYL LIGANDS; INTERMOLECULAR AMINATION; SELECTIVE FUNCTIONALIZATION; BIARYL COMPOUNDS; BONDS; ALKYLAMINES; ACCESS; COMPLEXES; MECHANISM;
D O I：
10.1002/anie.201812215
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Recent advances in (CpMIII)-M-x catalysis (M=Co, Rh, Ir) have enabled a variety of enantioselective C(sp(2))-H functionalization reactions, but enantioselective C(sp(3))-H functionalization is still largely unexplored. We describe an asymmetric C(sp(3))-H amidation of thioamides using an achiral Co-III/chiral carboxylic acid hybrid catalytic system, which provides easy and straightforward access to chiral beta-amino thiocarbonyl and beta-amino carbonyl building blocks with a quaternary carbon stereocenter.
引用
收藏
页码：1153 / 1157
页数：5
相关论文
共 50 条
  • [31] Cobalt-Catalyzed Enantio- and Regioselective C(sp3)-H Alkenylation of Thioamides
    Staronova, Lucia
    Yamazaki, Ken
    Xu, Xing
    Shi, Heyao
    Bickelhaupt, F. Matthias
    Hamlin, Trevor A.
    Dixon, Darren J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (13)
  • [32] Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Aminocyclopropanes
    Shi, Yongjia
    Yang, Yuhuan
    Xu, Senmiao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (19)
  • [33] Iridium-Catalyzed Enantioselective α-C(sp3)-H Borylation of Azacycles
    Chen, Lili
    Yang, Yuhuan
    Liu, Luhua
    Gao, Qian
    Xu, Senmiao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (28) : 12062 - 12068
  • [34] Cu catalyzed sp3 C-H amidation: Catalyst controlled site selectivity
    Warren, Timothy
    Bakhoda, Abolghasem
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [35] Synthesis of Sulfur-Stereogenic Sulfoximines via Co(III)/Chiral Carboxylic Acid-Catalyzed Enantioselective C-H Amidation
    Zhou, Yi-Bo
    Zhou, Tao
    Qian, Pu-Fan
    Li, Jun-Yi
    Shi, Bing-Feng
    ACS CATALYSIS, 2022, 12 (15) : 9806 - 9811
  • [36] Chiral Counteranion Strategy for Asymmetric Oxidative C(sp3)-H/C(sp3)-H Coupling: Enantioselective α-Allylation of Aldehydes with Terminal Alkenes
    Wang, Pu-Sheng
    Lin, Hua-Chen
    Zhai, Yu-Jia
    Han, Zhi-Yong
    Gong, Liu-Zhu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (45) : 12218 - 12221
  • [37] Nickel-Catalyzed Site-Selective Intermolecular C(sp3)-H Amidation
    Chen, Jinhong
    Wang, Hao
    Day, Craig S.
    Martin, Ruben
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (50)
  • [38] Rhodium(III)-Catalyzed Intermolecular Amidation with Azides via C(sp3)-H Functionalization
    Wang, Nuancheng
    Li, Renhe
    Li, Liubo
    Xu, Shansheng
    Song, Haibin
    Wang, Baiquan
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11): : 5379 - 5385
  • [39] Electrochemical Benzylic C(sp3)-H Direct Amidation
    Choi, Anthony
    Goodrich, Oliver H.
    Atkins, Alexander P.
    Edwards, Matthew D.
    Tiemessen, David
    George, Michael W.
    Lennox, Alastair J. J.
    ORGANIC LETTERS, 2024, 26 (03) : 653 - 657
  • [40] Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes
    Shi, Yongjia
    Gao, Qian
    Xu, Senmiao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (27) : 10599 - 10604
12345