Rhodium-Catalyzed Regio-, Diastereo-, and Enantioselective Three-Component Carboamination of Dienes via C-H Activation

被引：42
|
作者：
Mi, Ruijie [1 ]
Zhang, Xuepeng [1 ]
Wang, Jinlei [1 ]
Chen, Haohua [2 ]
Lan, Yu [2 ]
Wang, Fen [1 ]
Li, Xingwei [1 ]
机构：
[1] Shaanxi Normal Univ SNNU, Sch Chem & Chem Engn, Xian 710062, Peoples R China
[2] Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China
来源：
ACS CATALYSIS | 2021年 / 11卷 / 11期
关键词：
enantioselective C-H activation; three-component; diene; allyl; amination; ALKENES; BONDS; ARYL;
D O I：
10.1021/acscatal.1c01615
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Reported herein is the rhodium-catalyzed enantioselective three-component coupling of arene, diene, and dioxazolone that occurs via C-H activation en route to allyl intermediate. This carboamination reaction affords chiral allylic amines in 1,2-selectivity, E-selectivity, and enantioselectivity, with electrophilic amination of the pi-allyl species being both regio- and enantio-determining.
引用
收藏
页码：6692 / 6697
页数：6
相关论文
共 50 条
  • [21] A rhodium-catalyzed C-H activation/cycloisomerization tandem
    Aissa, Christophe
    Furstner, Alois
    1600, American Chemical Society, Columbus, OH 43210-3337, United States (129):
  • [22] Regio- and Stereoselective Rhodium(II)-Catalyzed C-H Functionalization of Cyclobutanes
    Garlets, Zachary J.
    Wertz, Benjamin D.
    Liu, Wenbin
    Voight, Eric A.
    Davies, Huw M. L.
    CHEM, 2020, 6 (01): : 304 - 313
  • [23] Construction of Axially Chiral Dialdehydes via Rhodium-Catalyzed Enantioselective C-H Amidation
    Yang, Jie-Ying
    Du, Ya-Ru
    Cheng, Fu-Qiang
    An, Kun
    Hu, Yuefei
    Li, Zhong-Yuan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (11)
  • [24] Co(III)-Catalyzed Three-Component Assembling of 2-Pyridones with Dienes and Formaldehyde via C-H Bond Activation
    Prusty, Priyambada
    Jeganmohan, Masilamani
    ORGANIC LETTERS, 2025, 27 (13) : 3210 - 3216
  • [25] Rhodium(III)-Catalyzed Three-Component Reaction of Imines, Alkynes, and Aldehydes through C-H Activation
    Huang, Ji-Rong
    Song, Qiang
    Zhu, Yu-Qin
    Qin, Liu
    Qian, Zhi-Yong
    Dong, Lin
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (51) : 16882 - 16886
  • [26] Diastereo- and Enantioselective Chemodivergent Three-Component Cascade Reactions via Gold and Carbene Sequential Catalysis
    Zhang, Shulei
    Wang, Shao-Jie
    Xin, Xiaolan
    Wang, Xia
    Tu, Zhifeng
    Lu, Shenci
    ACS CATALYSIS, 2024, 14 (12): : 9275 - 9282
  • [27] 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
  • [28] Rhodium-Catalyzed Atroposelective Construction of Indoles via C-H Bond Activation
    Sun, Lincong
    Chen, Haohua
    Liu, Bingxian
    Chang, Junbiao
    Kong, Lingheng
    Wang, Fen
    Lan, Yu
    Li, Xingwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (15) : 8391 - 8395
  • [29] Rhodium-catalyzed norbornenylation of 2-vinylpyridines via C-H activation
    Lim, YG
    Han, JS
    Kang, JB
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1998, 19 (11): : 1143 - 1145
  • [30] 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
12345