Auto-tandem catalysis: facile synthesis of substituted alkylidenecyclohexanones by domino (4+2) cycloaddition-elimination reaction

被引:12
|
作者
Takasu, Kiyosei [1 ]
Tanaka, Toru [1 ]
Azuma, Takumi [1 ]
Takemoto, Yoshiji [1 ]
机构
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068571, Japan
关键词
CASCADE;
D O I
10.1039/c0cc03336g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A catalytic domino reaction producing substituted 2-alkylidene-cyclohexanone from 3-oxymethyl-2-siloxy-1,3-butadienes, which can be prepared from Baylis-Hillman adducts, and alpha, beta-unsaturated ketones is described. The process involves two mechanistically distinct reactions, (4+2) cycloaddition and elimination. Both of these reactions are catalyzed by Tf2NH.
引用
收藏
页码:8246 / 8248
页数:3
相关论文
共 50 条
  • [21] REGIOSELECTIVITY IN THE [4+2] CYCLOADDITION OF BENZYNE - SYNTHESIS OF 11-SUBSTITUTED APORPHINES
    CASTEDO, L
    GUITIAN, E
    SAA, C
    SUAU, R
    SAA, JM
    TETRAHEDRON LETTERS, 1983, 24 (20) : 2107 - 2108
  • [22] Keggin heteropolyacid in auto-tandem catalysis: confinement effects over ordered mesoporous silica in the synthesis of 2-pyridones
    Galvan, Adriana
    Damian-Ascencio, Edgar
    Martinez, Merced
    Dominguez-Esquivel, Jose Manuel
    Vazquez, Miguel A.
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (17) : 8258 - 8267
  • [23] Synthesis of C-ring substituted xanthones from the [4+2] cycloaddition reaction of vinylchromones and acyclic enamines
    Kelkar, AS
    Letcher, RM
    Cheung, KK
    Chiu, KF
    Brown, RD
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (22): : 3732 - 3741
  • [24] A Facile and Efficient Synthesis of Dihydroisobenzofuran Derivatives via Tandem Palladium-Catalyzed Coupling, Propargyl-Allenyl Rearrangement, [4+2] Cycloaddition and Aromatization Reaction
    Shen, Ruwei
    Huang, Xian
    Chen, Lingzhu
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (18) : 2865 - 2870
  • [25] DABCO-catalyzed unusual [4+2] cycloaddition reaction: non-substituted allenoate acts as a four-carbon synthon and facile synthesis of spirooxindoles
    Liu, Yufen
    Du, Yanlong
    Yu, Aimin
    Mu, Haifeng
    Meng, Xiangtai
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (04) : 1226 - 1230
  • [26] Synthesis of New 4,4a-Dihydroxanthones via [4+2]-Cycloaddition Reaction
    Chernov, N. M.
    Moroz, T. V.
    Shutov, R. V.
    Kuz'mich, N. N.
    Shchegolev, A. E.
    Sopova, M. V.
    Yakovlev, I. P.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (12) : 2463 - 2470
  • [27] Synthesis of New 4,4a-Dihydroxanthones via [4+2]-Cycloaddition Reaction
    N. M. Chernov
    T. V. Moroz
    R. V. Shutov
    N. N. Kuz’mich
    A. E. Shchegolev
    M. V. Sopova
    I. P. Yakovlev
    Russian Journal of General Chemistry, 2019, 89 : 2463 - 2470
  • [28] Halogen bond catalysis of the [4+2] cycloaddition reaction of 2-alkenylindoles: catalytic modes and stereoselectivity
    Li, Ying
    Zhao, Chang
    Zhang, Huaiyu
    Zeng, Yanli
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2023, 26 (01) : 477 - 484
  • [29] Auto-Tandem Catalysis in Ionic Liquids: Synthesis of 2-Oxazolidinones by Palladium-Catalyzed Oxidative Carbonylation of Propargylic Amines in EmimEtSO4
    Mancuso, Raffaella
    Maner, Asif
    Ziccarelli, Ida
    Pomelli, Christian
    Chiappe, Cinzia
    Della Ca', Nicola
    Veltri, Lucia
    Gabriele, Bartolo
    MOLECULES, 2016, 21 (07)
  • [30] Synthesis of corrole-fullerene dyads via [4+2] cycloaddition reaction
    Li, Chengjie
    Zhang, Jie
    Liu, Xiujun
    Zhou, Yongzhu
    Sun, Dongming
    Cheng, Ping
    Zhang, Bao
    Feng, Yaqing
    RSC ADVANCES, 2014, 4 (77): : 40758 - 40762