Enantioselective Synthesis of Indole-Based Biaryl Atropisomers via Palladium-Catalyzed Dynamic Kinetic Intramolecular C-H Cyclization

被引：153
|
作者：
He, Congfa
Hou, Mengqing
Zhu, Zixi
Gu, Zhenhua [1 ]
机构：
[1] Univ Sci & Technol China, Dept Chem, 96 Jinzhai Rd, Hefei 230026, Anhui, Peoples R China
来源：
ACS CATALYSIS | 2017年 / 7卷 / 08期
关键词：
atropisomer; homogeneous catalysis; palladium; C-H cyclization; indole; AXIALLY CHIRAL BIARYLS; ASYMMETRIC TRANSFER HYDROGENATION; MIYAURA COUPLING REACTION; ATROPOSELECTIVE SYNTHESIS; 2+2+2 CYCLOADDITION; EFFICIENT SYNTHESIS; NATURAL-PRODUCTS; RESOLUTION; LIGANDS; OLEFINATION;
D O I：
10.1021/acscatal.7b01855
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：
We report here a palladium-catalyzed enantioselective synthesis of indole-based atropisomers via an intramolecular dynamic kinetic C-H cyclization. The TADDOL-derived phosphoramidite ligand proves to be most efficient in this directing-group-free transformation, delivering products with up to 96:4 er. The thermal stability of the axial chirality of the atropisomers has also been investigated.
引用
收藏
页码：5316 / 5320
页数：5
相关论文
共 50 条
  • [41] Enantioselective γ-Lactam Synthesis via Palladium-Catalyzed Intramolecular Asymmetric Allylic Alkylation
    Bantreil, Xavier
    Prestat, Guillaume
    Madec, David
    Fristrup, Peter
    Poli, Giovanni
    SYNLETT, 2009, (09) : 1441 - 1444
  • [42] Synthesis of Functionalized Spiroindolines via Palladium-Catalyzed Methine C-H Arylation
    Saget, Tanguy
    Perez, David
    Cramer, Nicolai
    ORGANIC LETTERS, 2013, 15 (06) : 1354 - 1357
  • [43] Synthesis of indoles, indolines, and carbazoles via palladium-catalyzed C-H activation
    Rago, Alexander J.
    Dong, Guangbin
    GREEN SYNTHESIS AND CATALYSIS, 2021, 2 (02): : 216 - 227
  • [44] Synthesis of Isoquinolinones via Regioselective Palladium-Catalyzed C-H Activation/Annulation
    Qi, Wenke
    Wu, Yimei
    Han, Yongxu
    Li, Yi
    CATALYSTS, 2017, 7 (11)
  • [45] Total synthesis of hebispeptin A and B via palladium-catalyzed C-H arylation
    Chen, Gong
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [46] Palladium-Catalyzed Directed Atroposelective C-H Iodination to Synthesize Axial Chiral Biaryl N-Oxides via Enantioselective Desymmetrization Strategy
    Yao, Linxi
    Woldegiorgis, Alemayehu Gashaw
    Huang, Shaoying
    Wang, Yongtao
    Lin, Xufeng
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (05)
  • [47] Monocarboxylation and Intramolecular Coupling of Butenylated Arenes via Palladium-Catalyzed C-H Activation Process
    Liu, Rui
    Lu, Ze-Hai
    Hu, Xiao-Hui
    Li, Jun-Li
    Yang, Xian-Jin
    ORGANIC LETTERS, 2015, 17 (06) : 1489 - 1492
  • [48] Palladium-Catalyzed Enantioselective C-H Olefination of Diaryl Sulfoxides through Parallel Kinetic Resolution and Desymmetrization
    Zhu, Yu-Chao
    Li, Yan
    Zhang, Bo-Chao
    Zhang, Feng-Xu
    Yang, Yi-Nuo
    Wang, Xi-Sheng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (18) : 5129 - 5133
  • [49] Palladium-catalyzed tandem C-H functionalization/cyclization strategy for the synthesis of 5 hydroxybenzofuran derivatives
    Ichake, Sachin
    Yao, Ching-Fa
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [50] Palladium-Catalyzed C-H Activation/Cyclization for the Synthesis of [60]Fullerene-Fused Phosphinolactones
    Liu, Qing-Song
    Qiu, Wen-Jie
    Niu, Chuang
    Wang, Guan-Wu
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (23): : 15754 - 15761
12345