Palladium-Catalyzed Enantioselective C-H Aminocarbonylation: Synthesis of Chiral Isoquinolinones

被引：48
|
作者：
Han, Hui [1 ,2 ]
Zhang, Tao [3 ]
Yang, Shang-Dong [2 ]
Lan, Yu [3 ,5 ]
Xia, Ji-Bao [1 ,4 ]
机构：
[1] Univ Chinese Acad Sci, Chinese Acad Sci, Suzhou Res Inst LICP, LICP,State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China
[2] Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China
[3] Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China
[4] Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[5] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Henan, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 06期
关键词：
OXIDATIVE CARBONYLATION; ALIPHATIC-AMINES; C(SP(3))-H BONDS; ACTIVATION; LIGANDS; FUNCTIONALIZATION; FERROCENES; IODINATION; DERIVATIVES; ALKYLATION;
D O I：
10.1021/acs.orglett.9b00315
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Pd-catalyzed enantioselective C-H carbonylation by desymmetrization was developed with commercially available L-pyroglutamic acid as chiral ligand. Isoquinolinones were successfully obtained with good yields and high enantioselectivities. Mechanistic studies and DFT calculations provided a reasonable reaction pathway.
引用
收藏
页码：1749 / 1754
页数：6
相关论文
共 50 条
  • [1] Synthesis of Isoquinolinones via Regioselective Palladium-Catalyzed C-H Activation/Annulation
    Qi, Wenke
    Wu, Yimei
    Han, Yongxu
    Li, Yi
    CATALYSTS, 2017, 7 (11)
  • [2] Enantioselective Synthesis of Chiral Isoindolines via Palladium-Catalyzed Asymmetric Allylic C-H Amination
    Chen, Yupeng
    Jin, Yangbin
    Li, Mingda
    Li, Jiarui
    Wu, Wanqing
    Jiang, Huanfeng
    CCS CHEMISTRY, 2024,
  • [3] Enantioselective synthesis of axially chiral vinyl arenes through palladium-catalyzed C-H olefination
    Sun, Qiao-Ying
    Ma, Wei-Yang
    Yang, Ke-Fang
    Cao, Jian
    Zheng, Zhan-Jiang
    Xu, Zheng
    Cui, Yu-Ming
    Xu, Li-Wen
    CHEMICAL COMMUNICATIONS, 2018, 54 (76) : 10706 - 10709
  • [4] Palladium-Catalyzed Enantioselective Isodesmic C-H Iodination
    Xu Senmiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (09) : 3325 - 3327
  • [5] Palladium-catalyzed enantioselective C-H functionalization via C-H palladation
    Zhan, Bei-Bei
    Jin, Liang
    Shi, Bing-Feng
    TRENDS IN CHEMISTRY, 2022, 4 (03): : 220 - 235
  • [6] Axially Chiral 2-Hydroxybiaryls by Palladium-Catalyzed Enantioselective C-H Activation
    Losada, Pablo
    Goicoechea, Laura
    Mascarenas, Jose Luis
    Gulias, Moises
    ACS CATALYSIS, 2023, 13 (21) : 13994 - 13999
  • [7] Palladium-Catalyzed Regioselective C-H Functionalization/Annulation Reaction of Amides and Allylbenzenes for the Synthesis of Isoquinolinones and Pyridinones
    Zhong, Rong
    Xu, Yong
    Sun, Manman
    Wang, Yurong
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (07): : 5255 - 5264
  • [8] Palladium-Catalyzed Oxidative Aminocarbonylation: A New Entry to Amides via C-H Activation
    Xie, Pan
    Xia, Chungu
    Huang, Hanmin
    ORGANIC LETTERS, 2013, 15 (13) : 3370 - 3373
  • [9] Palladium-Catalyzed Enantioselective Allylic Alkylations through C-H Activation
    Trost, Barry M.
    Thaisrivongs, David A.
    Donckele, Etienne J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) : 1523 - 1526
  • [10] Enantioselective Synthesis of N-N Atropisomers by Palladium-Catalyzed C-H Functionalization of Pyrroles
    Yao, Wang
    Lu, Chuan-Jun
    Zhan, Li-Wen
    Wu, Yi
    Feng, Jia
    Liu, Ren-Rong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (21)
12345