Synthesis of 3,3-Dialkyl-Substituted Isoindolinones Enabled by Nickel-Catalyzed Reductive Dicarbofunctionalization of Enamides

被引:34
|
作者
Fang, Ke [1 ,2 ]
Huang, Wenyi [1 ,2 ]
Shan, Chunxiao [1 ,2 ]
Qu, Jingping [1 ,2 ]
Chen, Yifeng [1 ,2 ]
机构
[1] East China Univ Sci & Technol, Feringa Nobel Prize Scientist Joint Res Ctr, Frontiers Sci Ctr Materiobiol & Dynam Chem, Sch Chem & Mol Engn,Key Lab Adv Mat, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Feringa Nobel Prize Scientist Joint Res Ctr, Frontiers Sci Ctr Materiobiol & Dynam Chem, Sch Chem & Mol Engn,Joint Int Res Lab Precis Chem, Shanghai 200237, Peoples R China
基金
上海市自然科学基金;
关键词
ARYL-ALKENYLATION;
D O I
10.1021/acs.orglett.1c01871
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein we report the nickel-catalyzed reductive dicarbofunctionalization of 1,1-disubstituted enamides with unactivated alkyl iodides to access the 3,3-dialkyl-substituted isoindolinone frameworks. This tandem cyclization/reductive coupling protocol exhibits broad functional group tolerance under mild conditions. The utilization of commercially accessible chiral Bn-Biox ligand allows excellent enantioselectivities to forge the tetrasubstituted stereocenters.
引用
收藏
页码:5523 / 5527
页数:5
相关论文
共 50 条
  • [31] STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED TETRAHYDROFURANS AND BUTYROLACTONES BY A NEW NICKEL-CATALYZED CARBOZINCATION
    VAUPEL, A
    KNOCHEL, P
    TETRAHEDRON LETTERS, 1994, 35 (45) : 8349 - 8352
  • [32] Chemoselective nickel-catalyzed hydrogenation: Synthesis of highly substituted aromatic amines
    Tom, Mai-Jan
    Miller, Paul
    Grange, Rebecca
    Esau, Derek
    Jerkiewicz, Gregory
    Evans, P. Andrew
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [33] Nickel-Catalyzed Asymmetric Synthesis of β- or β,γ-Substituted GABA Derivatives Enabled by Photoactive Ternary Electron Donor-Acceptor Complex
    Xie, Ying
    Lai, Ze-Min
    Chan, Albert S. C.
    Guo, Jing
    Lu, Gui
    ACS CATALYSIS, 2024,
  • [34] Nickel-Catalyzed Reductive Addition of Aryl/Benzyl Halides and Pseudohalides to Carbodiimides for the Synthesis of Amides
    Panahi, Farhad
    Jamedi, Fereshteh
    Iranpoor, Nasser
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (04) : 780 - 788
  • [35] Nickel-catalyzed reductive aminocarbonylation of vinyl triflates with nitro compounds for the synthesis of α,β-unsaturated amides
    Huo, Yong-Wang
    Yao, Lingyun
    Qi, Xinxin
    Wu, Xiao-Feng
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (24): : 6974 - 6978
  • [36] Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling
    Hofstra, Julie L.
    Cherney, Alan H.
    Ordner, Ciara M.
    Reisman, Sarah E.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (01) : 139 - 142
  • [37] Nickel-catalyzed reductive cross-coupling polymerization of dithiosulfonates and dibromides for the synthesis of polythioethers
    Yi, Xin
    Zeng, Hao
    Chen, Chunyu
    Luo, Ziwei
    Li, Ningyu
    Cen, Junyang
    Pan, Yuening
    Li, Ze
    Zhang, Pinglu
    POLYMER CHEMISTRY, 2025, 16 (13) : 1441 - 1447
  • [38] Synthesis of 3-propargyl isoindolinones by Pd/Cu-catalyzed enantioselective Heck/Sonogashira reaction of enamides
    Wang, Qiang
    Pan, Ya-Lin
    Liang, Ren-Xiao
    Hu, Yuan-Yuan
    Jia, Yi-Xia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (05) : 1073 - 1077
  • [39] CHEMICAL TRANSFORMATIONS OF DIOLS AND CYCLIC ETHERS .20. STUDY OF THERMAL DEGRADATION OF 3,3-DIALKYL-SUBSTITUTED OXETANES BY MICROREACTOR TECHNIQUE
    BARTOK, M
    KOZMA, B
    ACTA CHIMICA ACADEMIAE SCIENTARIUM HUNGARICAE, 1967, 52 (01): : 83 - &
  • [40] Photoredox/Nickel Dual-Catalyzed Stereoselective Synthesis of Distal Cyano-Substituted Enamides
    Lu, Xiao-Yu
    Wang, Jun-Chao
    Sun, Xiao-Mei
    Gao, Meng-Ting
    Ying, Weng-Jing
    Ge, Meng-Yuan
    Wei, Zheng-Huan
    Liu, Zi
    Chen, Xing-Ke
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (01): : 513 - 524