Phosphine-Catalyzed Substitution of Allenoates with Oxindoles: An Approach to 3-Allenic or 3-Dienoic Oxindoles

被引:0
作者
Yang, Ze-ren [1 ]
Gui, Hou-ze [2 ,3 ]
Shi, Min [1 ,2 ,3 ]
机构
[1] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem,Ctr Excellence Mo, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] East China Univ Sci & Technol, Key Lab Adv Mat, 130 Mei Long Rd, Shanghai 200237, Peoples R China
[3] East China Univ Sci & Technol, Inst Fine Chem, 130 Mei Long Rd, Shanghai 200237, Peoples R China
来源
CHEMISTRYSELECT | 2021年 / 6卷 / 36期
基金
中国国家自然科学基金;
关键词
Organocatalysis; nucleophilic substitution; allenes; ENANTIOSELECTIVE GAMMA-ADDITION; 3-ISOTHIOCYANATO OXINDOLES; ALLENES; ANNULATION; 2,3-BUTADIENOATES; CYCLOADDITION; CONSTRUCTION; NUCLEOPHILES; HETEROCYCLES; KETIMINES;
D O I
10.1002/slct.202102930
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new method for substitution of allenoate using oxindoles as nucleophilic reagents has been disclosed in this paper upon phosphine catalysis under mild conditions to afford 3-allenic or 3-dienoic oxindoles in moderate to good yields depending on the substituent at the aromatic ring of oxindole. According to the previous works, the plausible reaction mechanisms have been proposed.
引用
收藏
页码:9709 / 9713
页数:5
相关论文
共 47 条
  • [1] Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality
    Alonso, Jose M.
    Almendros, Pedro
    [J]. CHEMICAL REVIEWS, 2021, 121 (07) : 4193 - 4252
  • [2] [Anonymous], 2019, ANGEW CHEM, V131, P2880
  • [3] [Anonymous], 2015, ANGEW CHEM, V127, P13154
  • [4] [Anonymous], 2018, ANGEW CHEM, V130, P6707
  • [5] [Anonymous], 2013, ANGEW CHEM, V125, P5219
  • [6] Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C-N, C-C, and C-O Bonds
    Blieck, Remi
    Taillefer, Marc
    Monnier, Florian
    [J]. CHEMICAL REVIEWS, 2020, 120 (24) : 13545 - 13598
  • [7] A Straightforward Synthesis of Cyclobutenones via a Tandem Michael Addition/Cyclization Reaction of 2,3-Allenoates with Organozincs
    Chai, Guobi
    Wu, Shangze
    Fu, Chunling
    Ma, Shengming
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (11) : 3740 - 3743
  • [8] Chan W.-L., 2019, ANGEW CHEM INT EDIT, V131, P6326
  • [9] Phosphine-Catalyzed (3+2) Annulation of Isoindigos with Allenes: Enantioselective Formation of Two Vicinal Quaternary Stereogenic Centers
    Chan, Wai-Lun
    Tang, Xiaodong
    Zhang, Fuhao
    Quek, Glenn
    Mei, Guang-Jian
    Lu, Yixin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (19) : 6260 - 6264
  • [10] Catalytic Enantioselective Allenoate-Alkene [2+2] Cycloadditions
    Conner, Michael L.
    Xu, Yao
    Brown, M. Kevin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (10) : 3482 - 3485