A silver(I)-catalyzed intramolecular Ficini's [2+2] cycloaddition employing ynamides

被引:17
|
作者
Wang, Xiao-Na [1 ,2 ,3 ]
Ma, Zhi-Xiong [2 ,3 ]
Deng, Jun [2 ,3 ,4 ]
Hsung, Richard P. [2 ,3 ]
机构
[1] Zhengzhou Univ, Sch Pharmaceut Sci, Zhengzhou 450001, Henan, Peoples R China
[2] Univ Wisconsin, Div Pharmaceut Sci, Madison, WI 53705 USA
[3] Univ Wisconsin, Dept Chem, Sch Pharm, Madison, WI 53705 USA
[4] Tianjin Univ, Sch Pharmaceut Sci & Technol, Key Lab Modern Drug Delivery & High Efficiency, Tianjin 300072, Peoples R China
关键词
Intramolecular [2+2] cycloaddition; Ynamides; The Ficini reaction; AgNTf2; Electrocyclic ring-opening; COUPLING REACTIONS; ALKYNYL BROMIDES; CHIRAL YNAMIDES; BETA-KETOESTERS; DIELS-ALDER; YNAMINES; N; N-DIETHYLAMINOPROPYNE; STEREOSELECTIVITY; CYCLOHEXENONES; INTERMEDIATE;
D O I
10.1016/j.tetlet.2015.01.017
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An intramolecular [2+2] cycloaddition using N-sulfonyl substituted ynamides tethered to an enone motif is described here. This thermally driven [2+2] cycloaddition manifold can be catalyzed effectively using AgNTf2, and represents the first examples of an intramolecular Ficini reaction. Published by Elsevier Ltd.
引用
收藏
页码:3463 / 3467
页数:5
相关论文
共 50 条
  • [21] Investigations into the Mechanism of Inter- and Intramolecular Iron-Catalyzed [2+2] Cycloaddition of Alkenes
    Joannou, Matthew, V
    Hoyt, Jordan M.
    Chirik, Paul J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (11) : 5314 - 5330
  • [22] Ruthenium-catalyzed [2+2] cycloadditions of bicyclic alkenes and ynamides
    Villeneuve, K
    Riddell, N
    Tam, W
    TETRAHEDRON, 2006, 62 (16) : 3823 - 3836
  • [23] REACTION OF INTRAMOLECULAR AND INTERMOLECULAR [2+2]CYCLOADDITION AND [2+2]CYCLOREVERSION WITH PARTICIPANCE OF METHYLLAMBERTIANATE MOLECULE
    RALDUGIN, VA
    GRISHKO, VV
    BAGRYANSKAJA, IY
    GATILOV, YV
    SHAKIROV, MM
    SIBIRSKII KHIMICHESKII ZHURNAL, 1993, (01): : 69 - 74
  • [24] Synthesis of Cyclobutanones by Gold(I)-Catalyzed [2+2] Cycloaddition of Ynol Ethers with Alkenes
    Zanini, Margherita
    Cataffo, Andrea
    Echavarren, Antonio M.
    ORGANIC LETTERS, 2021, 23 (22) : 8989 - 8993
  • [25] INTRAMOLECULAR PHOTO[2+2]CYCLOADDITION OF 2-ALKENOYLOXYCYCLOHEX-2-ENONES
    IKEDA, M
    TAKAHASHI, M
    UCHINO, T
    TAMURA, Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1984, 32 (02) : 538 - 542
  • [26] Computational Study of Iron-Catalyzed Intramolecular [2+2] Cycloaddition and Cycloisomerization of Enyne Acetates: Mechanism and Selectivity
    Wang, Haoran
    Zhou, Qingyang
    Gao, Ailin
    Shang, Zhenfeng
    Li, Ruifang
    Xu, Xiufang
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (02): : 944 - 951
  • [27] PERISELECTIVITY IN THE BASE-CATALYZED INTRAMOLECULAR [2+2]-CYCLOADDITION REACTION OF 3-PHENYLSULFONYL-SUBSTITUTED PROPYNES
    PADWA, A
    LIPKA, H
    WATTERSON, SH
    TETRAHEDRON LETTERS, 1995, 36 (26) : 4521 - 4524
  • [28] Bridged Bicyclic γ-Sultams by Intramolecular Flow Photochemical [2+2] Cycloaddition
    Zaika, Yevhen O.
    Borodin, Illia O.
    Olekh, Heorhii O.
    Kovalov, Maksym V.
    Diachenko, Oleksandr D.
    Brovarets, Volodymyr S.
    Vashchenko, Bohdan V.
    Grygorenko, Oleksandr O.
    ORGANIC LETTERS, 2025, 27 (12) : 2858 - 2862
  • [29] [2+2]CYCLOADDITION OF NORBORNENES WITH ALKYNES CATALYZED BY RUTHENIUM COMPLEXES
    MITSUDO, T
    NARUSE, H
    KONDO, T
    OZAKI, Y
    WATANABE, Y
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (05): : 580 - 581
  • [30] ORGN 101-Intramolecular Gassman [2+2] cycloaddition reaction
    Ko, Changhong
    Ghosh, Sunil K.
    Hsung, Richard P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234