Construction of Bispirooxindole Heterocycles via Palladium-Catalyzed Ring-Opening Formal [3+2]-Cycloaddition of Spirovinylcyclopropyl Oxindole and 3-Oxindole Derivatives

被引:27
|
作者
Xiao, Jun-An [1 ]
Li, Yu-Chun [1 ]
Luo, Zhi-Jin [1 ]
Cheng, Xiu-Liang [1 ]
Deng, Zhi-Xiong [2 ]
Chen, Wen-Qiang [1 ]
Su, Wei [1 ]
Yang, Hua [2 ]
机构
[1] Nanning Normal Univ, Guangxi Key Lab Nat Polymer Chem & Phys, Nanning 530001, Peoples R China
[2] Cent S Univ, Coll Chem & Chem Engn, Changsha 410083, Hunan, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 04期
基金
中国国家自然科学基金;
关键词
DONOR-ACCEPTOR CYCLOPROPANE; DIELS-ALDER REACTIONS; 3+2 CYCLOADDITION; ENANTIOSELECTIVE CONSTRUCTION; DIASTEREOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; VINYL CYCLOPROPANES; STEREOCENTERS; ISATINS;
D O I
10.1021/acs.joc.8b02889
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed ring-opening oxo-formal [3 + 2]-cycloaddition reaction of novel donor-acceptor spirovinylcyclopropyl oxindole with 3-oxindole is described. The developed protocol provides facile access to oxo-bispirooxindole derivatives in good yields (up to 82% yield) with excellent diastereoselectivities (up to 20:1 dr).
引用
收藏
页码:2297 / 2306
页数:10
相关论文
共 50 条
  • [1] Palladium-catalysed ring-opening [3+2]-annulation of spirovinylcyclopropyl oxindole to diastereoselectively access spirooxindoles
    Xiao, Jun-An
    Cheng, Xiu-Liang
    Li, Yu-Chun
    He, Yi-Miao
    Li, Jin-Lian
    Liu, Zhi-Ping
    Xia, Peng-Ju
    Su, Wei
    Yang, Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (01) : 103 - 107
  • [2] Rapid Access to Spirocyclic Oxindole Alkaloids: Application of the Asymmetric Palladium-Catalyzed [3+2] Trimethylenemethane Cycloaddition
    Trost, Barry M.
    Bringley, Dustin A.
    Zhang, Ting
    Cramer, Nicolai
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (44) : 16720 - 16735
  • [3] Palladium-catalyzed asymmetric [3+2] cycloaddition to construct 1,3-indandione and oxindole-fused spiropyrazolidine scaffolds
    Cao, Bo
    Mei, Liang-Yong
    Li, Xiao-Ge
    Shi, Min
    RSC ADVANCES, 2015, 5 (112): : 92545 - 92548
  • [4] Diastereoselective Access to Seven-Membered Benzosultams via Palladium-Catalyzed Ring-Opening [3+2]-Annulation
    Xiao, Jun-An
    Zhang, Huan
    Luo, Xue-Ling
    Meng, Ru-Fang
    Wang, Wei
    Lu, Wei-dong
    Su, Wei
    Lin, Chenxiang
    Xia, Peng-Ju
    Yang, Hua
    ORGANIC LETTERS, 2023, 25 (22) : 4145 - 4149
  • [5] Diastereo- and Enantioselective Construction of Oxindole-Fused Spirotetrahydrofuran Scaffolds through Palladium-Catalyzed Asymmetric [3+2] Cycloaddition of Vinyl Cyclopropanes and Isatins
    Mei, Liang-yong
    Wei, Yin
    Xu, Qin
    Shi, Min
    ORGANOMETALLICS, 2013, 32 (12) : 3544 - 3556
  • [6] Palladium-Catalyzed [3+2] Cycloaddition of Activated Butadienylcyclopropanes
    Yang, Zhi-Xiong
    Wei, Yu-Qing
    Yang, Cun
    Li, Yun-Fan
    Ding, Chang-Hua
    Xu, Bin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (01)
  • [7] Palladium-Catalyzed [3+2] Cycloaddition of Vinylcyclopropane and Ketones
    Ding, Wen-Ping
    Du, Juan
    Liu, Xiu-Yan
    Chen, Di
    Ding, Chang-Hua
    Deng, Qing-Hai
    Hou, Xue-Long
    SYNLETT, 2019, 30 (08) : 947 - 950
  • [8] Palladium-catalyzed [3+2] cycloaddition of alkylidenecyclopropanes with imines
    Oh, BH
    Nakamura, I
    Saito, S
    Yamamoto, Y
    TETRAHEDRON LETTERS, 2001, 42 (35) : 6203 - 6205
  • [9] Regioselective synthesis of novel dispiropyrrolidine and dispiropyrrolizidine oxindole derivatives via azomethine ylide specific [3+2]-cycloaddition
    Lanka, Srinu
    Thennarasu, Sathiah
    Perumal, Paramasivan T.
    RSC ADVANCES, 2014, 4 (05): : 2263 - 2266
  • [10] Stereoselective Synthesis of Tropanes via a 6π-Electrocyclic Ring-Opening/ Huisgen [3+2]-Cycloaddition Cascade of Monocyclopropanated Heterocycles
    Sonnleitner, Carina M.
    Park, Saerom
    Eckl, Robert
    Ertl, Thomas
    Reiser, Oliver
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (41) : 18110 - 18115