Lewis acid-catalyzed [3+2] annulations of oxindole based spirocyclic donor-acceptor cyclopropanes with ynamides

被引：8
|
作者：
Zhang, Dongxin [1 ]
Cheng, Qihang [1 ]
Chen, Lvjia [1 ]
Deng, Huiqing [1 ]
Cai, Hu [1 ]
Zhang, Qian-Feng [1 ]
机构：
[1] Anhui Univ Technol, Inst Mol Engn & Appl Chem, 59 Hudong Rd, Maanshan 243002, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 44期
关键词：
BAYLIS-HILLMAN CARBONATES; DIASTEREOSELECTIVE CONSTRUCTION; ENANTIOSELECTIVE CONSTRUCTION; SPIROOXINDOLES; STRATEGY; ISATINS; DESIGN;
D O I：
10.1039/d1ob01922h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[3 + 2] annulations of oxindole based spirocyclic donor-acceptor cyclopropanes and ynamides catalyzed by copper triflate have been developed for the synthesis of biologically important spirocyclopenteneoxindoles. These reactions tolerated a wide scope of substrates and provided the desired products in good to high yields (up to 90%) with up to >40 : 1 diastereoselectivities under mild conditions.
引用
收藏
页码：9645 / 9648
页数：4
相关论文
共 50 条
  • [41] Copper Catalyzed [3+2] Annulation of Indoles with 1,1,2,2-Tetrasubstituted Donor-Acceptor Cyclopropanes
    Yan Wen-Guang
    Wang Pan
    Wang Lijia
    Sun Xiu-Li
    Tang Yong
    ACTA CHIMICA SINICA, 2017, 75 (08) : 783 - 787
  • [42] Lewis Acid-Catalyzed Formal (4+2)- and (2+2+2)-Cycloaddition Between 1-Azadienes and Styrylmalonates as Analogues of Donor-Acceptor Cyclopropanes
    Sergeev, Pavel G.
    Novikov, Roman A.
    Tomilov, Yury V.
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (23) : 5292 - 5299
  • [43] Triflic Acid-Catalyzed Cycloisomerization Reactions of Donor-Acceptor Cyclopropanes: Access to Alkyl 5-Arylfuran-2-carboxylates
    Zhu, Yuequan
    Xu, Panpan
    Gong, Yuefa
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (11): : 4829 - 4834
  • [44] Synthesis of Oxaspiranic Compounds through [3+2] Annulation of Cyclopropenones and Donor-Acceptor Cyclopropanes
    Rivero, Alexandra R.
    Fernandez, Israel
    Ramirez de Arellano, Carmen
    Sierra, Miguel A.
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02): : 1207 - 1213
  • [45] Substrate specific ring opening annulations of donor-acceptor cyclopropanes with 3-phenacylidene-2-oxindoles
    Pramanik, Sayan
    Saha, Pinaki
    Ghosh, Prasanta
    Mukhopadhyay, Chhanda
    TETRAHEDRON, 2023, 131
  • [46] Cyclopentene Synthesis by a Catalytic [3+2] Annulation of Donor-Acceptor Cyclopropanes with Polarized Alkenes
    Xu, Cong
    Wei, Na
    Zhu, Dongsheng
    Wang, Mang
    CHEMISTRYSELECT, 2020, 5 (36): : 11399 - 11402
  • [47] Lewis-Acid-Catalysed Tandem Meinwald Rearrangement/Intermolecular [3+2]-Cycloaddition of Epoxides with Donor-Acceptor Cyclopropanes: Synthesis of Functionalized Tetrahydrofurans
    Pandey, Ashok Kumar
    Ghosh, Asit
    Banerjee, Prabal
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (11) : 2517 - 2523
  • [48] Lewis acid-mediated reactions of donor-acceptor cyclopropanes with diazo esters
    R. A. Novikov
    D. D. Borisov
    Yu. V. Tomilov
    Russian Chemical Bulletin, 2018, 67 : 265 - 273
  • [49] Lewis acid-catalyzed (3+2) annulation of bicyclobutanes with ynamides: access to 2-amino-bicyclo[2.1.1]hexenes
    Sarkar, Deeptanu
    Deswal, Shiksha
    Das, Rohan Chandra
    Biju, Akkattu T.
    CHEMICAL SCIENCE, 2024, 15 (39) : 16243 - 16249
  • [50] Lewis acid-mediated reactions of donor-acceptor cyclopropanes with diazo esters
    Novikov, R. A.
    Borisov, D. D.
    Tomilov, Yu. V.
    RUSSIAN CHEMICAL BULLETIN, 2018, 67 (02) : 265 - 273
12345