Phosphine-Catalyzed [3+2] Cycloaddition of Aza-Aurones and Allenoates: Enantioselective Synthesis of 2-Spirocyclopentyl-Indolin-3-Ones

被引:3
|
作者
Brambilla, Elisa [1 ]
Pozza, Camilla [1 ]
Rizzato, Silvia [2 ]
Abbiati, Giorgio [1 ]
Pirovano, Valentina [1 ]
机构
[1] Univ Milan, Dipartimento Sci Farmaceut, Sez Chim Gen & Organ A Marchesini, Via G Venezian 21, I-20133 Milan, Italy
[2] Univ Milan, Dipartimento Chim, Via C Golgi 19, I-20133 Milan, Italy
关键词
asymmetric catalysis; cycloaddition; organocatalysis; phosphanes; spiro compounds; SUBSTITUTED ALLENOATES; ASYMMETRIC-SYNTHESIS; ANNULATION REACTION; NITRILE IMINES; BREVIANAMIDE-A; REGIOSELECTIVITY; ALKALOIDS; MECHANISM; ALLENES;
D O I
10.1002/ejoc.202201385
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective phosphine-catalyzed [3+2] cycloaddition between aza-aurones and allenoates is here described. The reaction proceeded under mild reaction conditions to afford 2-spirocyclopentyl indolin-3-one derivatives as single gamma-isomer and with high levels of stereocontrol.
引用
收藏
页数:5
相关论文
共 50 条
  • [1] Phosphine-catalyzed [3+2] cycloaddition of allenoates with trifluoromethylketones: synthesis of dihydrofurans and tetrahydrofurans
    Wang, Tong
    Ye, Song
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) : 5260 - 5265
  • [2] Phosphine-catalyzed enantioselective [3+2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones
    Zhou, Wei
    Wang, Huamin
    Tao, Mengna
    Zhu, Chao-Ze
    Lin, Tao-Yan
    Zhang, Junliang
    CHEMICAL SCIENCE, 2017, 8 (06) : 4660 - 4665
  • [3] Phosphine-Catalyzed [3+2] Annulations with γ-Methyl Allenoates
    Ma, Rong
    Song, Gege
    Xi, Qiuzhen
    Yang, Liu
    Li, Er-Qing
    Duan, Zheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (08) : 2196 - 2202
  • [4] Phosphine-catalyzed asymmetric [3+2] annulation of chalcones with allenoates for enantioselective synthesis of functionalized cyclopentenes
    Gao, Zhenzhen
    Wang, Chang
    Yuan, Chunhao
    Zhou, Leijie
    Sun, Zhanhu
    Xiao, Yumei
    Guo, Hongchao
    RSC ADVANCES, 2015, 5 (127): : 105359 - 105362
  • [5] Stereoselective synthesis of 2-spirocyclopropyl-indolin-3-ones through cyclopropanation of aza-aurones with tosylhydrazones
    Pirovano, Valentina
    Brambilla, Elisa
    Riva, Marika
    Leoni, Sara
    Rizzato, Silvia
    Garanzini, Davide
    Abbiati, Giorgio
    Rossi, Elisabetta
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (17) : 3925 - 3931
  • [6] Stereoselective synthesis of 2-spirocyclopropyl-indolin-3-ones through cyclopropanation of aza-aurones with tosylhydrazones
    Pirovano, Valentina
    Brambilla, Elisa
    Riva, Marika
    Leoni, Sara
    Rizzato, Silvia
    Garanzini, Davide
    Abbiati, Giorgio
    Rossi, Elisabetta
    Organic and Biomolecular Chemistry, 2021, 19 (17): : 3925 - 3931
  • [7] Divergent Phosphine-Catalyzed [2+4] or [3+2] Cycloaddition Reactions of γ-Substituted Allenoates with Oxadienes
    Li, Erqing
    Chang, Meijia
    Liang, Ling
    Huang, You
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (04) : 710 - 714
  • [8] Phosphine-Catalyzed [3+2] Cycloaddition and Vinylation of Indole-Derived α,α-Dicyanoolefins with γ-Substituted Allenoates
    Yuan, Chang
    Tan, Hao
    Jiang, Xue-Fei
    Liu, Si
    Jiang, Lu
    Cao, Qi-Ying
    Xu, Xing-Jie
    Deng, Xiao-Yan
    Pan, Guan-Nan
    Chen, Jian-Yang
    Cui, Hai-Lei
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (10) : 1893 - 1902
  • [9] Phosphine-Catalyzed Enantioselective Dearomative [3+2]-Cycloaddition of 3-Nitroindoles and 2-Nitrobenzofurans
    Wang, Huamin
    Zhang, Junyou
    Tu, Youshao
    Zhang, Junliang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (16) : 5422 - 5426
  • [10] Phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles and allenoates
    Liu, Kui
    Wang, Gang
    Cheng, Shao-Jie
    Jiang, Wen-Feng
    He, Cheng
    Ye, Zhi-Shi
    TETRAHEDRON LETTERS, 2019, 60 (29) : 1885 - 1890