RhI-Catalyzed Intramolecular [3+2] Cycloaddition of 1-Allene-vinylcyclopropanes

被引:7
|
作者
Liu, Cheng-Hang [1 ]
Li, Feng [1 ]
Yuan, Yuan [1 ]
Dou, Meng [1 ]
Yu, Zhi-Xiang [1 ]
机构
[1] Peking Univ, Coll Chem, Minist Educ, BNLMS,Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
基金
中国国家自然科学基金;
关键词
allenes; bicyclic compounds; cycloaddition; rhodium; vinylcyclopropanes; RH(I)-CATALYZED (3+2)+1 CYCLOADDITION; AMINO-SUBSTITUTED CYCLOPROPANES; BOND ACTIVATION; ENE-VINYLCYCLOPROPANES; 8-MEMBERED CARBOCYCLES; VINYL AZIRIDINES; FORMAL SYNTHESIS; ALKYNES; CO; METHYLENECYCLOPROPANES;
D O I
10.1002/ajoc.201800294
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rhodium-catalyzed intramolecular [3+2] cycloaddition of 1-allene-vinylcyclopropanes (1-allene-VCPs) to construct cyclopentane-embedded bicyclic structures with quaternary stereocenters at the bridgehead position has been developed with good to excellent yields. In addition, this transformation could also be conducted on a large scale with reduced catalyst loading, which could be useful for further derivatizations and applications.
引用
收藏
页码:1609 / 1613
页数:5
相关论文
共 50 条
  • [21] Asymmetric [3+2] Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Aldehydes by Synergistic Palladium and Organocatalysis
    Halskov, Kim Soholm
    Naesborg, Line
    Tur, Fernando
    Jorgensen, Karl Anker
    ORGANIC LETTERS, 2016, 18 (09) : 2220 - 2223
  • [22] Palladium-Catalyzed Diastereo- and Enantioselective [3+2] Cycloaddition of Vinylcyclopropanes with Azadienes: Efficient Access to Chiral Spirocycles
    Liu, Kai
    Yang, Jianfeng
    Li, Xiaoxun
    ORGANIC LETTERS, 2021, 23 (03) : 826 - 831
  • [23] INTRAMOLECULAR [3+2]-CYCLOADDITION OF NITRONES WITH ALLENES AND ALKYNES
    PADWA, A
    MESKE, M
    NI, ZJ
    TETRAHEDRON LETTERS, 1993, 34 (32) : 5047 - 5050
  • [24] INTRAMOLECULAR [3+2] NITRONE-ALKYNE CYCLOADDITION
    KANG, HY
    CHO, YS
    KOH, HY
    CHANG, MH
    TETRAHEDRON LETTERS, 1991, 32 (24) : 2779 - 2782
  • [25] Transformation of Anilines to 1-Azaspiro[4.5]decanes via Dearomatization and Palladium-Catalyzed aza-[3+2] Cycloaddition with Vinylcyclopropanes
    Xu, Tingxuan
    Hu, Jinhao
    He, Qiuqin
    Fan, Renhua
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [26] Comparative DFT study on the platinum catalyzed [3+2] and [2+2] cycloaddition reactions between the derivatives of allene and alkene
    Saha, Rohini
    Chatterjee, Arpita
    Mondal, Sonjoy
    Pal, Poulami
    Chakrabarty, Kuheli
    Das, Gourab Kanti
    COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2019, 1163
  • [27] Mechanistic Insights into the Ru(II)-Catalyzed Intramolecular Formal [3+2] Cycloaddition of (E)-1,6-Enynes
    Liu, Rui
    Chou, Yajie
    Lian, Bing
    Fang, De-cai
    Gao, Ming
    Cheng, Tanyu
    Liu, Guohua
    ORGANIC LETTERS, 2019, 21 (17) : 6815 - 6820
  • [28] Pt-Catalyzed Tandem 1,2-Acyloxy Migration/Intramolecular [3+2] Cycloaddition of Enynyl Esters
    Zheng, Huaiji
    Zheng, Jiyue
    Yu, Binxun
    Chen, Qiang
    Wang, Xiaolei
    He, Yongping
    Yang, Zhen
    She, Xuegong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) : 1788 - +
  • [29] Insertion of Imines into Vinylcyclopropanes Catalyzed by Nucleophilic Iron Complexes: A Formal [3+2]-Cycloaddition Strategy for the Synthesis of Substituted Pyrrolidine Derivatives
    Pursley, Dominik
    Plietker, Bernd
    SYNLETT, 2014, 25 (16) : 2316 - 2318
  • [30] Pd-catalyzed [3+2] cycloaddition of vinylcyclopropanes with 1-azadienes: synthesis of 4-cyclopentylbenzo[e][1,2,3]oxathiazine 2,2-dioxides
    Lin, Yan
    Wang, Qijun
    Wu, Yang
    Wang, Chang
    Jia, Hao
    Zhang, Cheng
    Huang, Jiaxing
    Guo, Hongchao
    RSC ADVANCES, 2018, 8 (71): : 40798 - 40803