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
  • [21] Synthesis of 8-azaprotosappanin A derivatives via intramolecular palladium-catalyzed ortho C-H activation/C-C cyclization and their antibacterial activity
    Zhou, Xuan
    Fu, Wanyong
    Jiang, Hongshuo
    Wang, Chenglong
    Ju, Chao
    Chu, Wenyi
    Sun, Zhizhong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (09) : 1955 - 1959
  • [22] Synthesis of Ferrocene Derivatives with Planar Chirality via Palladium-Catalyzed Enantioselective C-H Bond Activation
    Pi, Chao
    Cui, Xiuling
    Liu, Xiuyan
    Guo, Mengxing
    Zhang, Hanyu
    Wu, Yangjie
    ORGANIC LETTERS, 2014, 16 (19) : 5164 - 5167
  • [23] Synthesis of Biaryl Atropisomers via Site-Selective C-H Functionalization
    Genova, Jason C.
    Nicewicz, David A.
    ORGANIC LETTERS, 2025, 27 (08) : 1889 - 1894
  • [24] Synthesis of Tetracyclic Flavonoids via Palladium-Catalyzed Intramolecular Oxidative Cyclization
    Ayyagari, Narasimham
    Belani, Jitendra D.
    SYNLETT, 2014, 25 (16) : 2350 - 2354
  • [25] Enantioselective Synthesis of N-N Biaryl Atropisomers through Iridium(I)-Catalyzed C-H Alkylation with Acrylates
    Yin, Si-Yong
    Zhou, Qiansujia
    Liu, Chen-Xu
    Gu, Qing
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (37)
  • [26] Palladium-catalyzed intramolecular C-H acylation of indoles with thioester
    Liu, Min
    Liu, Yu-Wen
    Xu, Hui
    Dai, Hui-Xiong
    TETRAHEDRON LETTERS, 2019, 60 (39)
  • [27] Palladium-Catalyzed Synthesis of Dibenzophosphole Oxides via Intramolecular Dehydrogenative Cyclization
    Kuninobu, Yoichiro
    Yoshida, Takuya
    Takai, Kazuhiko
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18): : 7370 - 7376
  • [28] Total synthesis of (+)-camptothecin via an intramolecular palladium-catalyzed cyclization strategy
    Chavan, Subhash P.
    Pathak, Ashok B.
    Kalkote, Uttam R.
    SYNLETT, 2007, (17) : 2635 - 2638
  • [29] SYNTHESIS OF NITROGEN-HETEROCYCLES VIA PALLADIUM-CATALYZED INTRAMOLECULAR CYCLIZATION
    LAROCK, RC
    BABU, S
    TETRAHEDRON LETTERS, 1987, 28 (44) : 5291 - 5294
  • [30] Asymmetric Synthesis of β-Lactam via Palladium-Catalyzed Enantioselective Intramolecular C(sp3)-H Amidation
    Tong, Hua-Rong
    Zheng, Wenrui
    Lv, Xiaoyan
    He, Gang
    Liu, Peng
    Chen, Gong
    ACS CATALYSIS, 2020, 10 (01): : 114 - 120
12345