Divergent synthesis of oxindole derivatives via controllable reactions of isatin-derived para-quinone methides with sulfur ylides

被引：23
作者：
You, Yong [1 ]
Quan, Bao-Xue [2 ]
Wang, Zhen-Hua [1 ]
Zhao, Jian-Qiang [1 ]
Yuan, Wei-Cheng [1 ,2 ]
机构：
[1] Chengdu Univ, Inst Adv Study, Chengdu 610106, Peoples R China
[2] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 24期
关键词：
CATALYTIC 1,6-CONJUGATE ADDITION/AROMATIZATION; REVERSE-TRANSCRIPTASE INHIBITORS; ASYMMETRIC-SYNTHESIS; 3,3-DISUBSTITUTED OXINDOLES; ENANTIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATIONS; DESIGN; ACCESS; SPIROCYCLOPROPANATION; DEAROMATIZATION;
D O I：
10.1039/d0ob00979b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalyst-free and controllable reaction of isatin-derivedpara-quinone methides with sulfur ylides was developed. This protocol enables the divergent synthesis of two different valuable oxindole derivatives with a broad substrate scope and high stereoselectivities (up to >20 : 1 dr and only the (Z)-configuration).
引用
收藏
页码：4560 / 4565
页数：6
相关论文
共 61 条
  • [1] N-Heterocyclic carbene catalysed 1,6-hydrophosphonylation of p-quinone methides and fuchsones: an atom economical route to unsymmetrical diaryl- and triarylmethyl phosphonates
    Arde, Panjab
    Anand, Ramasamy Vijaya
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (24) : 5550 - 5554
  • [2] Badillo JJ, 2010, CURR OPIN DRUG DISC, V13, P758
  • [3] Recent advances in spirocyclization of indole derivatives
    Bariwal, Jitender
    Voskressensky, Leonid G.
    Van der Eycken, Erik V.
    [J]. CHEMICAL SOCIETY REVIEWS, 2018, 47 (11) : 3831 - 3848
  • [4] Catalytic asymmetric synthesis of polysubstituted spirocyclopropyl oxindoles: organocatalysis versus transition metal catalysis
    Cao, Zhong-Yan
    Zhou, Jian
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (07): : 849 - 858
  • [5] A New Organocatalytic Concept for Asymmetric α-Alkylation of Aldehydes
    Caruana, Lorenzo
    Kniep, Florian
    Johansen, Tore Kiilerich
    Poulsen, Pernille H.
    Jorgensen, Karl Anker
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (45) : 15929 - 15932
  • [6] DABCO-Catalyzed Michael/Alkylation Cascade Reactions Involving α-Substituted Ammonium Ylides for the Construction of Spirocyclopropyl Oxindoles: Access to the Powerful Chemical Leads against HIV-1
    Chen, Lin
    He, Jin
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (08) : 5203 - 5219
  • [7] Organocatalytic Asymmetric Assembly Reactions: Synthesis of Spirooxindoles via Organocascade Strategies
    Cheng, Daojuan
    Ishihara, Yoshihiro
    Tan, Bin
    Barbas, Carlos F., III
    [J]. ACS CATALYSIS, 2014, 4 (03): : 743 - 762
  • [8] A tandem Heck-carbocyclization/Suzuki-coupling approach to the stereoselective syntheses of asymmetric 3,3-(diarylmethylene)indolinones
    Cheung, WS
    Patch, RJ
    Player, MR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) : 3741 - 3744
  • [9] Asymmetric Catalytic 1,6-Conjugate Addition/Aromatization of para-Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic Centers
    Chu, Wen-Dao
    Zhang, Le-Fen
    Bao, Xu
    Zhao, Xian-He
    Zeng, Chao
    Du, Ji-Yuan
    Zhang, Guo-Biao
    Wang, Fang-Xin
    Ma, Xiao-Yan
    Fan, Chun-An
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9229 - 9233
  • [10] Bifunctional tertiary amine-squaramide catalyzed asymmetric catalytic 1,6-conjugate addition/aromatization of para-quinone methides with oxindoles
    Deng, Yu-Hua
    Zhang, Xiang-Zhi
    Yu, Ke-Yin
    Yan, Xu
    Du, Ji-Yuan
    Huang, Hanmin
    Fan, Chun-An
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (22) : 4183 - 4186
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