Ynol Ethers: Synthesis and Reactivity

被引:4
|
作者
Verrier, Charlie [1 ]
Carret, Sebastien [1 ]
Poisson, Jean-Francois [1 ]
机构
[1] Univ Grenoble Alpes, Dept Chim Mol SERCO, UMR 5250, CNRS,IMCG FR 2607, F-38041 Grenoble, France
关键词
Alkynes; Enol ethers; Ketenes; Synthesis; Ynol ethers; ACETYLENIC ETHERS; ALKYNYL ETHERS; INTRAMOLECULAR CARBOLITHIATION; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; 2+2 CYCLOADDITION; CHEMISTRY; CARBANIONS; REAGENTS; STRATEGY;
D O I
10.2533/chimia.2016.93
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ynol ethers are highly valuable substrates offering a wide range of reactivity. These highly electron rich heterosubstitued alkynes can be of great synthetic potential. In this mini-review, the different methods for the synthesis of ynol ethers are first presented, divided in three main approaches involving a beta-elimination, a carbene rearrangement and a direct oxidation of an alkyne. Their reactivity is then summarized underlying their synthetic utility. This non-exhaustive review aims at presenting the intrinsic reactivity of these compounds, still underexploited in synthesis.
引用
收藏
页码:93 / 96
页数:4
相关论文
共 50 条
  • [21] Radical addition to ynol ethers - A convenient procedure for the stereoselective preparation of α-iodo enol ethers in neutral conditions
    Longpre, Fanny
    Rusu, Natalia
    Larouche, Maxime
    Hanna, Rana
    Daoust, Benoit
    CANADIAN JOURNAL OF CHEMISTRY, 2008, 86 (10) : 970 - 975
  • [22] Ynol Ethers from Dichloroenol Ethers: Mechanistic Elucidation Through 35CI Labeling
    Darses, Benjamin
    Milet, Anne
    Philouze, Christian
    Greene, Andrew E.
    Poisson, Jean-Francois
    ORGANIC LETTERS, 2008, 10 (20) : 4445 - 4447
  • [23] [2+2+1] cycloadditions of ynol ethers. The synthesis of iron complexes of 3-alkoxycyclopentadienones
    Imbriglio, JE
    Rainier, JD
    TETRAHEDRON LETTERS, 2001, 42 (40) : 6987 - 6990
  • [24] A Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl Ynol Ethers as Key Building Blocks
    Zhang, Wenhan
    Ready, Joseph M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (33) : 10684 - 10692
  • [25] Gold(I)-Catalyzed Intermolecular Formal [4+2] Cycloaddition of O-Aryl Ynol Ethers and Enol Ethers: Synthesis of Chromene Derivatives
    Suarez-Rodriguez, Tatiana
    Suarez-Sobrino, angel L.
    Ballesteros, Alfredo
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (51) : 13079 - 13084
  • [27] One-Pot Reaction of Carboxylic Acids, Ynol Ethers, and m-CPBA for Synthesis of α-Carbonyloxy Esters
    Zeng, Linwei
    Sajiki, Hironao
    Cui, Sunliang
    ORGANIC LETTERS, 2019, 21 (16) : 6423 - 6426
  • [28] HOTf-Catalyzed, Solvent-Free Oxyarylation of Ynol Ethers and Thioethers
    Hu, Liang
    Gui, Qngwen
    Chen, Xiang
    Tan, Ze
    Zhu, Gangguo
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (11): : 4861 - 4868
  • [29] Synthesis of γ,δ-Unsaturated Esters and Amides via Au(I)-Catalyzed Reactions of Aryl Ynol Ethers or Ynamides with Allylic Alcohols
    Misawa, Souta
    Miyairi, Asaki
    Oonishi, Yoshihiro
    Nolan, Steven P.
    Sato, Yoshihiro
    SYNTHESIS-STUTTGART, 2021, 53 (24): : 4644 - 4653
  • [30] Regioselective and Stereoselective Entry to β,β-Disubstituted Vinyl Ethers via the Sequential Hydroboration/Suzuki-Miyaura Coupling of Ynol Ethers
    Cui, Weijian
    Mao, Mengyi
    He, Zuying
    Zhu, Gangguo
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19): : 9815 - 9821