Asymmetric Synthesis of Spirooxindoles via Organocascade Strategies

被引:10
|
作者
Xiao, Yonglong [1 ]
Zhou, Yu [2 ]
Wang, Jiang [2 ]
Wang, Jiaxin [1 ]
Liu, Hong [2 ]
机构
[1] China Pharmaceut Univ, Jiangsu Prov Key Lab Drug Design & Optimizat Med, Nanjing 210009, Jiangsu, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China
基金
中国国家自然科学基金;
关键词
spirooxindoles; asymmetric; catalysis; organocascade; N-HETEROCYCLIC CARBENE; HIGHLY ENANTIOSELECTIVE SYNTHESIS; 6-MEMBERED SPIROCYCLIC OXINDOLES; BAYLIS-HILLMAN CARBONATES; 1,3-DIPOLAR CYCLOADDITION; CONSECUTIVE STEREOCENTERS; STEREOSELECTIVE-SYNTHESIS; PHOSPHINES SYNTHESIS; 3+2 ANNULATION; FACILE ACCESS;
D O I
10.6023/cjoc201504045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The spirooxindoles have broad and promising activities in various therapeutic areas, and become a privileged skeleton for drug discovery. Therefore, the development of some simple and efficient strategies to build these sophisticated scaffolds has become one of the most widespread concerns. However, the traditional methods are limited by the separation and purification of intermediates, the functional group protection and de-protection. Recently, the cascade strategies have shown special advantages in the synthesis of optically active natural products and complex molecules, many related studies have been reported. This review summarizes the enantioselective synthesis of spirooxindoles via cascade strategies in the past five years and organized on the basis of four types of starting materials: unsaturated oxindole derivatives, C(3)-substituted oxindoles, C(3)-unsubstituted oxindoles and nonoxindoles.
引用
收藏
页码:2035 / 2048
页数:14
相关论文
共 57 条
  • [31] Cinchona-based Primary Amine Catalysis in the Asymmetric Functionalization of Carbonyl Compounds
    Melchiorre, Paolo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (39) : 9748 - 9770
  • [32] Asymmetric enamine catalysis
    Mukherjee, Santanu
    Yang, Jung Woon
    Hoffmann, Sebastian
    List, Benjamin
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5471 - 5569
  • [33] Tertiary Amine-Catalyzed Chemoselective and Asymmetric [3+2] Annulation of Morita-Baylis-Hillman Carbonates of Isatins with Propargyl Sulfones
    Peng, Jing
    Huang, Xin
    Jiang, Lin
    Cui, Hai-Lei
    Chen, Ying-Chun
    [J]. ORGANIC LETTERS, 2011, 13 (17) : 4584 - 4587
  • [34] Asymmetric Synthesis of 3,3′-Spirooxindoles Fused with Cyclobutanes through Organocatalytic Formal [2+2] Cycloadditions under H-Bond-Directing Dienamine Activation
    Qi, Liang-Wen
    Yang, Yu
    Gui, Yong-Yuan
    Zhang, Yong
    Chen, Feng
    Tian, Fang
    Peng, Lin
    Wang, Li-Xin
    [J]. ORGANIC LETTERS, 2014, 16 (24) : 6436 - 6439
  • [35] Enantioselective Assembly of Spirocyclic Oxindole-dihydropyranones through NHC-Catalyzed Cascade Reaction of Isatins with N-Hydroxybenzotriazole Esters of α,β-Unsaturated Carboxylic Acid
    Que, Yonglei
    Li, Tuanjie
    Yu, Chenxia
    Wang, Xiang-Shan
    Yao, Changsheng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (06): : 3289 - 3294
  • [36] Spiroindolones, a Potent Compound Class for the Treatment of Malaria
    Rottmann, Matthias
    McNamara, Case
    Yeung, Bryan K. S.
    Lee, Marcus C. S.
    Zou, Bin
    Russell, Bruce
    Seitz, Patrick
    Plouffe, David M.
    Dharia, Neekesh V.
    Tan, Jocelyn
    Cohen, Steven B.
    Spencer, Kathryn R.
    Gonzalez-Paez, Gonzalo E.
    Lakshminarayana, Suresh B.
    Goh, Anne
    Suwanarusk, Rossarin
    Jegla, Timothy
    Schmitt, Esther K.
    Beck, Hans-Peter
    Brun, Reto
    Nosten, Francois
    Renia, Laurent
    Dartois, Veronique
    Keller, Thomas H.
    Fidock, David A.
    Winzeler, Elizabeth A.
    Diagana, Thierry T.
    [J]. SCIENCE, 2010, 329 (5996) : 1175 - 1180
  • [37] Temporal activation of p53 by a specific MDM2 inhibitor is selectively toxic to tumors and leads to complete tumor growth inhibition
    Shangary, Sanjeev
    Qin, Dongguang
    McEachern, Donna
    Liu, Meilan
    Miller, Rebecca S.
    Qiu, Su
    Nikolovska-Coleska, Zaneta
    Ding, Ke
    Wang, Guoping
    Chen, Jianyong
    Bernard, Denzil
    Zhang, Jian
    Lu, Yipin
    Gu, Qingyang
    Shah, Rajal B.
    Pienta, Kenneth J.
    Ling, Xiaolan
    Kang, Sanmao
    Guo, Ming
    Sun, Yi
    Yang, Dajun
    Wang, Shaomeng
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2008, 105 (10) : 3933 - 3938
  • [38] Facile Access to Functionalized Spiro[indoline-3,2′-pyrrole]-2,5′-diones via Post-Ugi Domino Buchwald-Hartwig/Michael Reaction
    Sharma, Nandini
    Li, Zhenghua
    Sharma, Upendra K.
    Van der Eycken, Erik V.
    [J]. ORGANIC LETTERS, 2014, 16 (15) : 3884 - 3887
  • [39] Lewis Acid Catalyzed Unprecedented [3+2] Cycloaddition Yields 3,3′-Pyrrolidinyldispirooxindoles Containing Four Contiguous Chiral Stereocenters with Two Contiguous Quaternary Spirostereocenters
    Suman, Koorathota
    Srinu, Lanka
    Thennarasu, Sathiah
    [J]. ORGANIC LETTERS, 2014, 16 (14) : 3732 - 3735
  • [40] Organocatalytic Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Azlactones and Methyleneindolinones
    Sun, Wangsheng
    Zhu, Gongming
    Wu, Chongyang
    Li, Guofeng
    Hong, Liang
    Wang, Rui
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (33) : 8633 - 8637