Tunable Gold(I)-Catalyzed [4+3] Cycloaddition for Divergent Synthesis of Furan-Fused N,O-Heterocycles

被引：33
|
作者：
Zhang, Shouzhi [1 ]
Tang, Aijie [1 ]
Chen, Panpan [1 ]
Zhao, Zhiqiang [1 ]
Miao, Maozhong [1 ]
Ren, Hongjun [1 ,2 ]
机构：
[1] Zhejiang Sci Tech Univ, Hangzhou, Peoples R China
[2] Taizhou Univ, Taizhou, Peoples R China
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 03期
关键词：
DIASTEREOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; 1-(1-ALKYNYL)CYCLOPROPYL KETONES; 3-COMPONENT REACTION; CATALYZED REACTIONS; ALLENYL KETONES; GOLD CARBENES; METAL; 2-(1-ALKYNYL)-2-ALKEN-1-ONES; NUCLEOPHILES; GENERATION;
D O I：
10.1021/acs.orglett.9b04312
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
By choosing suitable ligand-directed gold catalysts, two types of gold-containing all-carbon 1,4-dipoles could be generated selectively from the gold(I)-catalyzed cycloisomerizations of allenyl ketones bearing a cyclopropyl moiety, which undergo [4 + 3] cycloadditions with nitrones to produce two regiomers of furan-condensed N,O-seven-membered rings in moderate to excellent yields highly selectively.
引用
收藏
页码：848 / 853
页数：6
相关论文
共 50 条
  • [1] Gold-catalyzed synthesis of N,O-heterocycles
    Hashmi, A. Stephen K.
    PURE AND APPLIED CHEMISTRY, 2010, 82 (03) : 657 - 668
  • [2] Stereoselective access to furan-fused [5.5.0] bicyclic heterocycles enabled by gold-catalyzed asymmetric [8+4] cycloaddition
    Wang, Xunhua
    Wang, Jianhua
    Li, Xiaoxun
    ORGANIC CHEMISTRY FRONTIERS, 2024, 12 (01): : 159 - 166
  • [3] Diastereospecific Gold(I)-Catalyzed Cyclization Cascade for the Controlled Preparation of N- and N,O-Heterocycles
    Muratore, Michael E.
    Konovalov, Andrey I.
    Armengol-Relats, Helena
    Echavarren, Antonio M.
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (58) : 15613 - 15621
  • [4] Gold catalyzed transannular [4+3] cycloaddition reactions
    Craft, Derek T.
    Bailey, Lauren
    Gung, Benjamin W.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [5] Synthesis of N-heterocycles via [4+3] cycloaddition of azomethine imine
    Sau, Madan
    Verma, Kshitiz
    Das, Tapas
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (11) : 3722 - 3734
  • [6] Synthesis of benzonorcaradienes by gold(I)-catalyzed [4+3] annulation
    Gorin, David J.
    Dube, Pascal
    Toste, F. Dean
    Journal of the American Chemical Society, 2006, 128 (45): : 14480 - 14481
  • [7] Synthesis of Daucane Natural Products Enabled by a Gold(I)-Catalyzed Tandem Cycloisomerization/(4+3) Cycloaddition
    Marti, Alex
    Armengol-Relats, Helena
    Sadurni, Anna
    Perez-Puigdomenech, Miquel A.
    Echavarren, Antonio M.
    ORGANIC LETTERS, 2025, 27 (10) : 2305 - 2309
  • [8] Synthesis of benzonorcaradienes by gold(I)-catalyzed [4+3] annulation
    Gorin, David J.
    Dube, Pascal
    Toste, F. Dean
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (45) : 14480 - 14481
  • [9] [4+3] Cycloaddition of ketenimines with furocarbenoids: Divergent and efficient synthesis of fused cycloheptatriene and tropone scaffolds
    Wang, Jin
    Li, Zhaoyang
    Bai, Shengxin
    Zhou, Qinghua
    Wu, Tengteng
    Hu, Zhongyan
    Xu, Xianxiu
    CHINESE CHEMICAL LETTERS, 2023, 34 (05)
  • [10] Gold-catalyzed transannular [4+3] cycloaddition reactions
    Gung, Benjamin W.
    Craft, Derek T.
    TETRAHEDRON LETTERS, 2009, 50 (22) : 2685 - 2687
12345