Synthesis of oxa-bridged carbocycles via rhodium/Lewis acid catalyzed [3 + 3] and [4 + 3] cycloadditions of carbonyl ylides with donor–acceptor strained carbocycles

被引：0
|
作者：
Li, Jiale [1 ]
Wang, Lingfei [1 ]
Liu, Pei-Nian [1 ,2 ]
Li, Xingguang [1 ]
机构：
[1] Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai,200237, China
[2] State Key Laboratory of Natural Medicines, School of Pharmacy, China Pharmaceutical University, Nanjing,210009, China
来源：
Organic Chemistry Frontiers | / 12卷 / 02期
基金：
中国国家自然科学基金;
关键词：
Catalysis; -; Cycloaddition;
D O I：
10.1039/d4qo01831a
中图分类号：
学科分类号：
摘要：
A method for cooperative rhodium/Lewis acid-catalyzed [3 + 3] and [4 + 3] cycloadditions of carbonyl ylides with donor–acceptor (D–A) strained carbocycles is described. It affords access to a wide range of structurally diverse oxa-bridged carbocycles with high efficiency and stereoselectivity. This method operates under mild conditions, exhibits good step and atom economy, and can be extended to [3 + 2] cycloadditions with D–A 1,2-dipoles, enabling the construction of oxa-bridged spirocycles. © the Partner Organisations 2025.
引用
下载
收藏
页码：491 / 496
相关论文
共 50 条
  • [1] Gold(I)-Catalyzed Cascade Cycloadditions between Allenamides and Carbonyl-Tethered Alkenes: An Enantioselective Approach to Oxa-Bridged Medium-Sized Carbocycles
    Faustino, Helio
    Alonso, Isaac
    Mascarenas, Jose L.
    Lopez, Fernando
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (25) : 6526 - 6530
  • [2] (3+3)-Annulation of Carbonyl Ylides with Donor-Acceptor Cyclopropanes: Synergistic Dirhodium(II) and Lewis Acid Catalysis
    Petzold, Martin
    Jones, Peter G.
    Werz, Daniel B.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (19) : 6225 - 6229
  • [3] Construction of Oxo-Bridged Diazocines via Rhodium-Catalyzed (4+3) Cycloaddition of Carbonyl Ylides with Azoalkenes
    Pang, Qiwen
    Zhou, Jin
    Wu, Yuling
    Zhou, Wu-Jingyun
    Zuo, Wei-Fang
    Zhan, Gu
    Han, Bo
    ORGANIC LETTERS, 2022, 24 (06) : 1362 - 1366
  • [4] Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes
    Mloston, Grzegorz
    Kowalczyk, Mateusz
    Augustin, Andre U.
    Jones, Peter G.
    Werz, Daniel B.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (46) : 6250 - 6253
  • [5] Synthesis of Various Bridged Ring Systems via Rhodium-Catalyzed Bridged (3+2) Cycloadditions
    He, Yu-Tao
    Li, Li-Xuan
    Lin, Xiaohong
    Hou, Bao-Long
    Li, Chuang-Chuang
    ORGANIC LETTERS, 2022, 24 (01) : 186 - 190
  • [6] Lewis Acid/Rhodium-Catalyzed Formal [3+3]-Cycloaddition of Enoldiazoacetates with Donor-Acceptor Cyclopropanes
    Cheng, Qing-Qing
    Qian, Yu
    Zavalij, Peter Y.
    Doyle, Michael P.
    ORGANIC LETTERS, 2015, 17 (14) : 3568 - 3571
  • [7] Access to [4,3,1]-Bridged Carbocycles via Rhodium(III)-Catalyzed C-H Activation of 2-Arylindoles and Annulation with Quinone Monoacetals
    Zheng, Guangfan
    Duan, Xujing
    Chen, Lu
    Sun, Jiaqiong
    Zhai, Shuailei
    Li, Xiaojiao
    Jing, Jierui
    Li, Xingwei
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (06): : 4543 - 4552
  • [8] Diastereoselective Synthesis of Cycloheptannelated Indoles via Lewis-Acid-Catalyzed (4+3)-Cyclization of Donor-Acceptor Cyclopropanes
    Li, Bao Qiong
    Qiu, Zong-Wang
    Ma, Ai Jun
    Peng, Jin-Bao
    Feng, Na
    Du, Ji-Yuan
    Pan, Han-Peng
    Zhang, Xiang-Zhi
    Xu, Xue-Tao
    ORGANIC LETTERS, 2020, 22 (05) : 1903 - 1907
  • [9] Highly regio- and stereoselective [3+2] cycloaddition of carbonyl ylides with imines: A novel entry to oxa-bridged piperidinone ring systems
    Muthusamy, S
    Krishnamurthi, J
    Suresh, E
    SYNLETT, 2005, (19) : 3002 - 3004
  • [10] Lewis acid-catalyzed [3+3] cycloadditions of donor-acceptor aziridines with N,N-dialkyl-3-vinylanilines via carbon-carbon bond cleavage
    Lee, Sang Gyu
    Kim, Sung-Gon
    TETRAHEDRON, 2018, 74 (27) : 3671 - 3678
12345