Metal Catalysis versus Organocatalysis in the Catalytic Asymmetric Synthesis of 3-Hydroxyoxindole

被引:29
作者
Liu, Yunlin [1 ]
Zhu, Feng [1 ]
Wang, Cuihong [1 ]
Zhou, Jian [1 ]
机构
[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
基金
中国国家自然科学基金;
关键词
3-substituted-3-hydroxyoxindole; asymmetric catalysis; metal catalysis; organocatalysis; BAYLIS-HILLMAN REACTION; HIGHLY ENANTIOSELECTIVE SYNTHESIS; FRIEDEL-CRAFTS REACTION; ALDOL REACTION; ARYLBORONIC ACIDS; STEREOSELECTIVE-SYNTHESIS; UNACTIVATED KETONES; SUBSTITUTED ISATINS; QUATERNARY CARBON; CONVOLUTAMYDINE E;
D O I
10.6023/cjoc201303038
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Substituted 3-hydroxyoxindoles are widely encountered in a large number of natural products, drugs and pharmaceutically active compounds. The catalytic asymmetric construction of this privileged skeleton has attracted great attention from synthetic chemistry, and much progress has been made in recent years. This review summarizes the advances in the catalytic enantioselective synthesis of four important types of subunits of 3-substituted 3-hydroxyoxindoles, and focuses on the discussion of the differences and advantages of metal catalysis and organocatalysis.
引用
收藏
页码:1595 / 1615
页数:21
相关论文
共 122 条
  • [51] Synthesis of Novel Enantiopure Biphenyl P,N-Ligands and Application in Palladium-Catalyzed Asymmetric Addition of Arylboronic Acids to N-Benzylisatin
    Lai, Hongshan
    Huang, Zhiyan
    Wu, Qiong
    Qin, Yong
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01) : 283 - 288
  • [52] Asymmetric Nitroaldol Reactions of Nitroalkanes with Isatins Catalyzed by Bifunctional Cinchona Alkaloid Derivatives
    Li, Mei-Qiu
    Zhang, Jin-Xin
    Huang, Xiao-Fei
    Wu, Bin
    Liu, Zhao-Min
    Chen, Jian
    Li, Xiang-Dong
    Wang, Xing-Wang
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (27) : 5237 - 5241
  • [53] Organocatalytic Enantioselective Stereoablative Hydroxylation of 3-Halooxindoles: An Effective Method for the Construction of Enantioenriched 3-Substituted 3-Hydroxy-2-Oxindoles
    Liao, Yu-Hua
    Wu, Zhi-Jun
    Han, Wen-Yong
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (29) : 8916 - 8920
  • [54] Gelsemine: A thought-provoking target for total synthesis
    Lin, H
    Danishefsky, SJ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (01) : 36 - 51
  • [55] Proline-catalyzed direct asymmetric aldol reactions
    List, B
    Lerner, RA
    Barbas, CF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) : 2395 - 2396
  • [56] Asymmetric cross aldol addition of isatins with α,β-unsaturated ketones catalyzed by a bifunctional Bronsted acid-Bronsted base organocatalyst
    Liu, Guo-Gui
    Zhao, Hua
    Lan, Yu-Bao
    Wu, Bin
    Huang, Xiao-Fei
    Chen, Jian
    Tao, Jing-Chao
    Wang, Xing-Wang
    [J]. TETRAHEDRON, 2012, 68 (20) : 3843 - 3850
  • [57] Regioselectivity-Reversed Asymmetric Aldol Reaction of 1,3-Dicarbonyl Compounds
    Liu, Hongxin
    Wu, Huayue
    Luo, Zhenli
    Shen, Jie
    Kang, Guowei
    Liu, Bidai
    Wan, Zhifu
    Jiang, Jun
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (38) : 11899 - 11903
  • [58] Catalytic Enantioselective Henry Reactions of Isatins: Application in the Concise Synthesis of (S)-(-)-Spirobrassinin
    Liu, Lu
    Zhang, Shilei
    Xue, Fei
    Lou, Guangshun
    Zhang, Haoyi
    Ma, Shichao
    Duan, Wenhu
    Wang, Wei
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (28) : 7791 - 7795
  • [59] Liu Y.-L., 2013, CHEM COMMUN, V49, P2022
  • [60] Primary 1,2-Diamine Catalysis (V): Efficient Asymmetric Aldol Reactions of Isatins with Cyclohexanone
    Liu, Yi
    Gao, Pengchao
    Wang, Junfeng
    Sun, Qi
    Ge, Zemei
    Li, Runtao
    [J]. SYNLETT, 2012, (07) : 1031 - 1034