Organocatalytic C-C bond activation of cyclopropenones for ring-opening formal [3+2] cycloaddition with isatins

被引:40
|
作者
Xu, Junyu [1 ]
Cao, Jing [1 ]
Fang, Chao [1 ]
Lu, Tao [1 ]
Du, Ding [1 ]
机构
[1] China Pharmaceut Univ, Dept Organ Chem, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 04期
基金
中国国家自然科学基金;
关键词
CARBON-CARBON BOND; CARBENE-CATALYZED REACTIONS; CPCO-MEDIATED REACTIONS; DIELS-ALDER ADDUCT; ALKYNYL ALDEHYDES; ACCESS; ANNULATION; 1,3-DIPHENYLISOBENZOFURAN; DIPHENYLCYCLOPROPENONE; SPIROOXINDOLES;
D O I
10.1039/c6qo00734a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclopropenones were first applied as potential 3C synthons in ring-opening formal cycloaddition via an organocatalytic C-C bond activation strategy. This [3 + 2] cycloaddition of cyclopropenones with isatins catalyzed by using two different Lewis bases offers rapid access to spirooxindoles 3 and 4 regioselectively. These findings will provide helpful guidelines for further investigation of the reactivity of cyclopropenones with organocatalysis.
引用
收藏
页码:560 / 564
页数:5
相关论文
共 50 条
  • [21] Copper-Catalyzed Ring-Opening (3+2) Annulation of Cyclopropenones with Ketoxime Acetates: Access to 1,2-Dihydro-pyrrol-3-ones Bearing a Quaternary Carbon Center
    Wang, Zhen-Hua
    Yang, Ping
    Zhang, Yan-Ping
    You, Yong
    Zhao, Jian-Qiang
    Zhou, Ming-Qiang
    Yuan, Wei-Cheng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (18)
  • [22] Investigation of C-C Bond Activation of sp-sp2 C-C Bonds of Acetylene Derivatives via Photolysis of Pt Complexes
    Gunay, Ahmet
    Brennessel, William W.
    Jones, William D.
    ORGANOMETALLICS, 2015, 34 (11) : 2233 - 2239
  • [23] Synthesis of Aromatic Compounds by Catalytic C-C Bond Activation of Biphenylene or Angular [3]Phenylene
    Korotvicka, Ales
    Cisarova, Ivana
    Roithova, Jana
    Kotora, Martin
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (14) : 4200 - 4207
  • [24] Carbonylative Formal Cycloaddition between Alkylarenes and Aldimines Enabled by Palladium-Catalyzed Double C-H Bond Activation
    Ding, Yongzheng
    Wu, Jianing
    Huang, Hanmin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (09) : 4982 - 4988
  • [25] Catalytic Double [2+2] Cycloaddition Relay Enabled C-C Triple Bond Cleavage of Yne-Allenones
    Li, Heng
    Hao, Wen-Juan
    Wang, Mian
    Qin, Xue
    Tu, Shu-Jiang
    Zhou, Peng
    Li, Guigen
    Wang, Jianyi
    Jiang, Bo
    ORGANIC LETTERS, 2018, 20 (14) : 4362 - 4366
  • [26] Rh(III)-Catalyzed Ring-Opening Addition of Azabenzonorbornadienes with Cyclic N-Sulfony Ketimines via C-H Bond Activation
    Zhang, Xuexin
    Gao, Yang
    Chen, Jingchao
    Fan, Ruifeng
    Shi, Guangrui
    He, Zhenxiu
    Fan, Baomin
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (19) : 4495 - 4499
  • [27] Computational, Mechanistic, and Experimental Insights into Regioselective Catalytic C-C Bond Activation in Linear 1-Aza-[3]triphenylene
    Ulc, Jan
    Asanuma, Yuya
    Moss, Robert
    Manca, Gabriele
    Cisarova, Ivana
    Kotora, Martin
    ACS OMEGA, 2022, 7 (10): : 8665 - 8674
  • [28] Highly Enantioselective Organocatalytic Michael Addition/Cyclization Cascade Reaction of Ylideneoxindoles with Isothiocyanato Oxindoles: A Formal [3+2] Cycloaddition Approach to Optically Active Bispirooxindole Derivatives
    Tan, Fen
    Cheng, Hong-Gang
    Feng, Bin
    Zou, You-Quan
    Duan, Shu-Wen
    Chen, Jia-Rong
    Xiao, Wen-Jing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (11) : 2071 - 2075
  • [29] Rhodium-Catalyzed Regioselective Carboacylation of Olefins: A C-C Bond Activation Approach for Accessing Fused-Ring Systems
    Xu, Tao
    Dong, Guangbin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (30) : 7567 - 7571
  • [30] Pd(<sc>ii</sc>)-catalyzed regioselective ring opening/[3+2] annulation reaction of enaminones with cyclopropenones: divergent synthesis of γ-butenolides and γ-lactams
    Zhang, Zhilai
    Xu, Yu
    Peng, Menglin
    Song, Siyu
    Wei, Yuanzheng
    Hu, Huimin
    Wang, Xiuju
    Yu, Fuchao
    CHEMICAL COMMUNICATIONS, 2024, 60 (100) : 14968 - 14971