Enantioselective synthesis of 3,3′-dihydropyrryl-spirooxindoles via an organocatalytic three-component reaction

被引:48
作者
Wei, Wen-Tao [1 ]
Chen, Chun-Xia [1 ]
Lu, Rui-Jiong [1 ]
Wang, Jin-Jia [1 ]
Zhang, Xue-Jing [1 ]
Yan, Ming [1 ]
机构
[1] Sun Yat Sen Univ, Inst Drug Synth & Pharmaceut Proc, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
MULTICOMPONENT REACTIONS; CONSTRUCTION; SPIROOXINDOLES; ISOCYANOESTERS; DOMINO; STEREOCENTERS; DISCOVERY;
D O I
10.1039/c2ob25629k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An organocatalytic three-component reaction of isatins, malononitrile and isocyanoacetates provided 3,3'-dihydropyrryl-spirooxindoles in excellent yields and enantioselectivities. The products could be readily converted to valuable 3,3'-pyrrolidinyl-spirooxindoles.
引用
收藏
页码:5245 / 5252
页数:8
相关论文
共 31 条
  • [1] Cooperative Catalysis for the First Asymmetric Formal [3+2] Cycloaddition Reaction of Isocyanoacetates to α,β-Unsaturated Ketones
    Arroniz, Carlos
    Gil-Gonzalez, Alberto
    Semak, Vladislav
    Escolano, Carmen
    Bosch, Joan
    Amat, Mercedes
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (20-21) : 3755 - 3760
  • [2] Badillo JJ, 2010, CURR OPIN DRUG DISC, V13, P758
  • [3] 1,3-Dicarbonyl compounds in stereoselective domino and multicomponent reactions
    Bonne, Damien
    Coquerel, Yoann
    Constantieux, Thierry
    Rodriguez, Jean
    [J]. TETRAHEDRON-ASYMMETRY, 2010, 21 (9-10) : 1085 - 1109
  • [4] Enantioselective Michael/Cyclization Reaction Sequence: Scaffold-Inspired Synthesis of Spirooxindoles with Multiple Stereocenters
    Cao, Yiming
    Jiang, Xianxing
    Liu, Luping
    Shen, Fangfang
    Zhang, Futing
    Wang, Rui
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) : 9124 - 9127
  • [5] Asymmetic Organocatalytic 1,3-Dipolar Cycloaddition of Azomethine Ylide to Methyl 2-(2-Nitrophenyl)acrylate for the Synthesis of Diastereoisomers of Spirotryprostatin A
    Chang, Mou-Nuo
    Wang, Hao
    Gong, Liu-Zhu
    [J]. ORGANIC LETTERS, 2011, 13 (09) : 2418 - 2421
  • [6] Highly Enantioselective Construction of Spiro[4H-pyran-3,3′-oxindoles] Through a Domino Knoevenagel/Michael/Cyclization Sequence Catalyzed by Cupreine
    Chen, Wen-Bing
    Wu, Zhi-Jun
    Pei, Qing-Lan
    Cun, Lin-Feng
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    [J]. ORGANIC LETTERS, 2010, 12 (14) : 3132 - 3135
  • [7] Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity
    Chen, Xiao-Hua
    Wei, Qiang
    Luo, Shi-Wei
    Xiao, Han
    Gong, Liu-Zhu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) : 13819 - 13825
  • [8] Recent developments in isocyanide based multicomponent reactions in applied chemistry
    Dömling, A
    [J]. CHEMICAL REVIEWS, 2006, 106 (01) : 17 - 89
  • [9] Asymmetric organocatalytic domino reactions
    Enders, Dieter
    Grondal, Christoph
    Huettl, Matthias R. M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) : 1570 - 1581
  • [10] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents
    Galliford, Chris V.
    Scheidt, Karl A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) : 8748 - 8758