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
  • [1] Rh-Catalyzed Formal [3+2] Cycloaddition Reactions with Cyclopropenones via Sequential C-H/C-C Bond Activation
    Qu, Qing-Long
    Ren, Yu-Tong
    Cao, Jun-Tao
    Sun, Wei
    Sun, Meng
    ORGANIC LETTERS, 2025, 27 (08) : 1967 - 1972
  • [2] Ag(I)-Catalyzed [3+2]-Annulation of Cyclopropenones and Formamides via C-C Bond Cleavage
    Ren, Jiang-Tao
    Wang, Jia-Xin
    Tian, Hu
    Xu, Jing-Lei
    Hu, Hong
    Aslam, Muhammad
    Sun, Meng
    ORGANIC LETTERS, 2018, 20 (21) : 6636 - 6639
  • [3] Silver-catalyzed ring-opening [3+2] annulation of cyclopropenones with amides
    Matsuda, Takanori
    Tabata, Yuki
    Suzuki, Hirotsugu
    NEW JOURNAL OF CHEMISTRY, 2018, 42 (23) : 19178 - 19182
  • [4] Rh(I)-catalyzed ring-opening of cyclobutanols via C-C bond activation: Synthesis of cis-olefin with a remote aldehyde
    Nie, Yu
    Chen, Jianzhong
    Zhang, Wanbin
    TETRAHEDRON, 2019, 75 (39)
  • [5] Organocatalytic Regiodivergent C-C Bond Cleavage of Cyclopropenones: A Highly Efficient Cascade Approach to Enantiopure Heterocyclic Frameworks
    Cao, Jian
    Fang, Ran
    Liu, Jin-Yu
    Lu, Hong
    Luo, Yong-Chun
    Xu, Peng-Fei
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (71) : 18863 - 18867
  • [6] Switchable selectivity in Pd- catalyzed [3+2] annulations of γ-oxy-2-cycloalkenones with 3-oxoglutarates: C-C/C-C vs C-C/O-C bond formation
    Liu, Yang
    Oble, Julie
    Poli, Giovanni
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 1107 - 1115
  • [7] Rh(iii)-Catalyzed spiroannulation of ketimines with cyclopropenones via sequential C-H/C-C bond activation
    Hu, Hong
    Li, Bin-Shi
    Xu, Jing-Lei
    Sun, Wei
    Wang, Yong
    Sun, Meng
    CHEMICAL COMMUNICATIONS, 2022, 58 (30) : 4743 - 4746
  • [8] Chemoselective C-C σ-Bond Activation of the Most Stable Ring in Biphenylene**
    Kong, Richard Y.
    Crimmin, Mark R.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (05) : 2619 - 2623
  • [9] Phosphine-catalyzed activation of cyclopropenones: a versatile C3 synthon for (3+2) annulations with unsaturated electrophiles
    He, Xin
    Ma, Pengchen
    Tang, Yuhai
    Li, Jing
    Shen, Shenyu
    Lear, Martin J.
    Houk, K. N.
    Xu, Silong
    CHEMICAL SCIENCE, 2022, 13 (43) : 12769 - 12775
  • [10] Enantioselective palladium-catalyzed C(sp2)-C(sp2) σ bond activation of cyclopropenones by merging desymmetrization and (3+2) spiroannulation with cyclic 1,3-diketones
    Zhou, Han-Qi
    Gu, Xing-Wei
    Zhou, Xiao-Hua
    Li, Li
    Ye, Fei
    Yin, Guan-Wu
    Xu, Zheng
    Xu, Li-Wen
    CHEMICAL SCIENCE, 2021, 12 (41) : 13737 - 13743
12345