Atroposelective Synthesis of N-N Axially Chiral Bipyrroles via Rhodium-Catalyzed C-H Insertion Reaction

被引:20
|
作者
Wang, Changkai [1 ]
Sun, Jiangtao [1 ]
机构
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China
关键词
ENANTIOSELECTIVE SYNTHESES; ATROPISOMERS; CONSTRUCTION; ARYLATION; ACCESS;
D O I
10.1021/acs.orglett.3c01509
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An atroposelective synthesis of bipyrroleswith an axially chiralN-N bond has been established via a rhodium-catalyzed C-Hbond insertion reaction to provide the desired atropisomers in goodyields (up to 97% yield) with good to excellent enantioselectivities(up to 99% ee).
引用
收藏
页码:4808 / 4812
页数:5
相关论文
共 50 条
  • [41] Diastereoselective synthesis of tetrahydropyridines via rhodium-catalyzed C-H bond activation
    Lu, Colin
    Duttwyler, Simon
    Ellman, Jonathan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [42] N-tosyloxycarbamates as reagents in rhodium-catalyzed C-H Amination reactions
    Huard, Kim
    Lebel, Helene
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (20) : 6222 - 6230
  • [43] Organocatalytic diastereo- and atroposelective construction of N-N axially chiral pyrroles and indoles
    Wang, Shao-Jie
    Wang, Xia
    Xin, Xiaolan
    Zhang, Shulei
    Yang, Hui
    Wong, Ming Wah
    Lu, Shenci
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [44] Multicomponent Synthesis of Iminocoumarins via Rhodium-Catalyzed C-H Bond Activation
    Chen, Zhan
    Jin, Shengnan
    Jiang, Wenyao
    Zhu, Feimin
    Chen, Yuqi
    Zhao, Yingwei
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (16): : 11006 - 11013
  • [45] Rhodium-Catalyzed Atroposelective C-H/C-H Cross-Coupling Reaction between 1-Aryl Isoquinoline Derivatives and Indolizines
    Zhang, Wen-Wen
    Liu, Chen-Xu
    Yang, Pusu
    Zhang, Su-Zhen
    Gu, Qing
    You, Shu-Li
    ORGANIC LETTERS, 2022, 24 (02) : 564 - 569
  • [46] Asymmetric rhodium-catalyzed click cycloaddition to access C-N axially chiral N-triazolyl indoles
    Zhou, Li
    Li, Yankun
    Li, Shunian
    Shi, Zhenwei
    Zhang, Xue
    Tung, Chen-Ho
    Xu, Zhenghu
    CHEMICAL SCIENCE, 2023, 14 (19) : 5182 - 5187
  • [47] Rhodium catalyzed synthesis of isoindolinones via C-H activation of N-benzoylsulfonamides
    Zhu, Chen
    Falck, John R.
    TETRAHEDRON, 2012, 68 (45) : 9192 - 9199
  • [48] Synthesis of axially chiral biaryl-2-carboxamidesthrough Pd(II)-catalyzed atroposelective C-H olefination
    Jiang, Bo-Yang
    Zhou, Gang
    Jiang, Ao-Lian
    Zhou, Tao
    Shi, Bing-Feng
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (13): : 3710 - 3716
  • [49] Rhodium-Catalyzed Atroposelective C-H Alkylation of 1-Aryl Isoquinoline Derivatives with Cyclopropanols
    Zhang, Wen-Wen
    Wang, Quannan
    Zheng, Chao
    You, Shu-Li
    ACS CATALYSIS, 2025, 15 (05): : 4017 - 4024
  • [50] Spirolactone syntheses through a rhodium-catalyzed intramolecular C-H insertion reaction: model studies towards the synthesis of syringolides
    Villalobos, Mauricio Navarro
    Wood, John L.
    TETRAHEDRON LETTERS, 2009, 50 (47) : 6450 - 6453