Phosphine-catalyzed [3+2] cycloaddition of ethyl buta-2,3-dienoate to adamantane-containing N-substituted maleimides

被引：6
|
作者：
Abel, Anton S. [1 ]
Averin, Alexei D. [1 ]
Savelyev, Evgenii N. [2 ]
Orlinson, Boris S. [2 ]
Novakov, Ivan A. [2 ]
Beletskaya, Irina P. [1 ]
机构：
[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia
[2] Volgograd State Tech Univ, Volgograd 400005, Russia
来源：
MENDELEEV COMMUNICATIONS | 2017年 / 27卷 / 06期
基金：
俄罗斯基础研究基金会; 俄罗斯科学基金会;
关键词：
CHIRAL PHOSPHINES; ANNULATION; ALLENES; CYCLOPENTENES; CONSTRUCTION; CARBONATES; CHEMISTRY; IMIDES;
D O I：
10.1016/j.mencom.2017.11.003
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Triphenylphosphine-catalyzed [3 + 2] cycloaddition between ethyl buta-2,3-dienoate and adamantane-containing N-substituted maleimides affords substituted bicycle succinimides in excellent yields.
引用
收藏
页码：550 / 552
页数：3
相关论文
共 27 条
  • [1] Phosphine-catalysed [3+2] cycloaddition of ethyl buta-2,3-dienoate and 4-quinolone-1,3-dicarboxylate
    Al-Soud, Yaseen A.
    Al-Masoudi, Najim A.
    Hass, Thomas
    Beifuss, Uwe
    LETTERS IN ORGANIC CHEMISTRY, 2008, 5 (01) : 55 - 56
  • [2] Phosphine-Catalyzed [3+2] Cycloaddition of 4,4-Dicyano-2-methylenebut-3-enoates with Benzyl Buta-2,3-dienoate and Penta-3,4-dien-2-one
    Zhang, Xiao-Nan
    Shi, Min
    ACS CATALYSIS, 2013, 3 (04): : 507 - 512
  • [3] Phosphine-catalyzed [3+2] cycloaddition of Morita—Baylis—Hillman carbonates to isothiocyanates in the synthesis of adamantane-containing trisubstituted aminothiophenes
    I. S. Zenkov
    A. S. Abel
    A. D. Averin
    G. M. Butov
    I. P. Beletskaya
    Russian Chemical Bulletin, 2021, 70 : 880 - 884
  • [4] 2-(Acetoxymethyl)buta-2,3-dienoate, a Versatile 1,4-Biselectrophile for Phosphine-Catalyzed (4+n) Annulations with 1,n-Bisnucleophiles (n=1, 2)
    Zhang, Qiongmei
    Yang, Lei
    Tong, Xiaofeng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (08) : 2550 - +
  • [5] Phosphine-catalyzed [3+2] cycloaddition of Morita-Baylis-Hillman carbonates to isothiocyanates in the synthesis of adamantane-containing trisubstituted aminothiophenes
    Zenkov, I. S.
    Abel, A. S.
    Averin, A. D.
    Butov, G. M.
    Beletskaya, I. P.
    RUSSIAN CHEMICAL BULLETIN, 2021, 70 (05) : 880 - 884
  • [6] Copper(I)-Catalyzed, One-Pot Synthesis of Multisubstituted Indoles from 2-Iodoanilines and Ethyl Buta-2,3-dienoate
    Wang, Xianxue
    Liu, Jin
    Guo, Han
    Ma, Chao
    Gao, Xiai
    Zhou, Kang
    Huang, Guosheng
    SYNTHESIS-STUTTGART, 2012, 44 (07): : 1037 - 1042
  • [7] Rhodium(I)-catalyzed [3+2+2]-cyclization of alkenyl Fischer carbene complexes with methyl buta-2,3-dienoate
    Barluenga, Jose
    Vicente, Ruben
    Lopez, Luis A.
    Tomas, Miguel
    TETRAHEDRON, 2010, 66 (33) : 6335 - 6339
  • [8] Phosphine-Catalyzed Stereospecific and Enantioselective Desymmetrizative [3+2] Cycloaddition of MBH Carbonates and N-(2-tert-Butylphenyl)maleimides
    Hou, Jie
    Hao, Wei
    Chen, Ying
    Wang, Zhen
    Yao, Weijun
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (12): : 9068 - 9077
  • [9] Phosphine-Catalyzed Atroposelective Formal [3+2] Cycloaddition Desymmetrization of N-Arylmaleimides
    Wang, Huamin
    Wei, Yibo
    Li, Yuqiang
    Long, Shuangshuang
    Sun, Li-Juan
    Li, Shixiong
    Lin, Ying-Wu
    ORGANIC LETTERS, 2022, 24 (36) : 6494 - 6498
  • [10] Phosphine-Catalyzed [3+2] Cycloaddition and Vinylation of Indole-Derived α,α-Dicyanoolefins with γ-Substituted Allenoates
    Yuan, Chang
    Tan, Hao
    Jiang, Xue-Fei
    Liu, Si
    Jiang, Lu
    Cao, Qi-Ying
    Xu, Xing-Jie
    Deng, Xiao-Yan
    Pan, Guan-Nan
    Chen, Jian-Yang
    Cui, Hai-Lei
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (10) : 1893 - 1902
123