Highly Substituted Cyclohexenes via Phosphine-Catalyzed [4+2] Annulation of Electron-deficient Dienes and Vinyl Ketones

被引:7
|
作者
Chen, Peng [1 ]
Zhang, Junyou [1 ]
Zhang, Junliang [1 ]
机构
[1] East China Normal Univ, Sch Chem & Mol Engn, Shanghai Key Lab Green Chem & Chem Proc, 3663 N Zhongshan Rd, Shanghai 200062, Peoples R China
基金
中国国家自然科学基金;
关键词
4+2] annulation; electron-deficient diene; Vinyl Ketone; Phosphine catalyst; Cyclohexene; FUNCTIONALIZED CYCLOPENTENES; ENANTIOSELECTIVE SYNTHESIS; ACTIVATED ALKENES; ASYMMETRIC-SYNTHESIS; 3+2 CYCLOADDITIONS; CYCLIZATION; ALLENOATES; OLEFINS; ALLENES; DESIGN;
D O I
10.1002/adsc.201701168
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A highly efficient phosphine-catalyzed [4+2] annulation of electron-deficient diene and alkyl vinyl ketone was developed for the first time, which provides an easy access to functionalized cyclohexenes. This method has the advantages of mild reaction conditions, widely functional group tolerance, high yields and transition metal free.
引用
收藏
页码:682 / 685
页数:4
相关论文
共 50 条
  • [1] Phosphine-catalyzed [4+2] annulation: Synthesis of cyclohexenes
    Tran, Yang S.
    Kwon, Ohyun
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) : 12632 - +
  • [2] Facile Synthesis of Spirooxindole-Cyclohexenes via Phosphine-Catalyzed [4+2] Annulation of α-Substituted Allenoates
    Chen, Rongshun
    Fan, Xia
    Xu, Zhaozhong
    He, Zhengjie
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (09) : 1469 - 1473
  • [3] Synthesis of novel electron-deficient chromone-fused dienes via phosphine catalyzed [4+2] annulation
    Waldmann, Herbert
    Bruss, Hanna
    Dueckert, Heiko
    Kumar, Kamal
    [J]. TETRAHEDRON LETTERS, 2011, 52 (17) : 2265 - 2267
  • [4] Phosphine-Catalyzed Internal Redox [4+2] Annulation between 1,4-Enynoates and Electron-Deficient Alkenes
    Li, Dongqiu
    Cheng, Fang
    Tang, Yuhai
    Li, Jing
    Li, Yang
    Jiao, Jiao
    Xu, Silong
    [J]. ORGANIC LETTERS, 2021, 23 (23) : 9030 - 9035
  • [5] An expedient phosphine-catalyzed [4+2] annulation: Synthesis of highly functionalized tetrahydropyridines
    Zhu, XF
    Lan, J
    Kwon, O
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (16) : 4716 - 4717
  • [6] Asymmetric Dearomatization of Electron-Deficient Heteroarenes by a Phosphine-Catalyzed [3+2] Annulation with Vinylcyclopropanes
    Dai, Xuan
    Zhang, Fuhao
    Dai, Lei
    Lu, Yixin
    [J]. CCS CHEMISTRY, 2023, 5 (09): : 2023 - 2032
  • [7] Phosphine-catalyzed bishydrophosphorylation of electron-deficient alkynes
    Salin, Alexey V.
    Il'in, Anton V.
    Faskhutdinov, Rustem I.
    Fayzullin, Robert R.
    [J]. TETRAHEDRON, 2019, 75 (18) : 2676 - 2686
  • [8] Phosphine-Catalyzed Enantioselective [4+2] Annulation of o-Quinone Methides with Allene Ketones
    Wang, Zhen
    Wang, Tianli
    Yao, Weijun
    Lu, Yixin
    [J]. ORGANIC LETTERS, 2017, 19 (15) : 4126 - 4129
  • [9] Diastereoselective Synthesis of 6-Trifluoromethyl-5,6-dihydropyrans via Phosphine-Catalyzed [4+2] Annulation of α-Benzylallenoates with Ketones
    Wang, Tong
    Ye, Song
    [J]. ORGANIC LETTERS, 2010, 12 (18) : 4168 - 4171
  • [10] Phosphine-Catalyzed [4+2] Annulations of 2-Alkylallenoates and Olefins: Synthesis of Multisubstituted Cyclohexenes
    Tran, Yang S.
    Martin, Tioga J.
    Kwon, Ohyun
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (08) : 2100 - 2105