N-Heterocyclic Carbene-Catalyzed Silyl Enol Ether Formation^†

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Abstract

N-Heterocyclic carbenes (NHCs) were found to catalyze the silyl transfer from trialkylsilyl ketene acetals to ketones. In the presence of a catalytic amount of NHC 3 (IAd, 0.1 to 5 mol %), a series of enolizable ketones as well as cyclohexanecarboxaldehyde were efficiently converted into the corresponding silyl enol ethers at 23 °C in THF.

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This article has been cited by 8 ACS Journal articles (5 most recent appear below).

• 

  Catalytic Formation of Silyl Enol Ethers and Its Applications for Aldol-Type Condensation and Aminomethylation Reactions

  Ruili Gao and Chae S. Yi
  ACS Catalysis2011 Article ASAP

  • Catalytic Formation of Silyl Enol Ethers and Its Applications for Aldol-Type Condensation and Aminomethylation Reactions

    Ruili Gao and Chae S. Yi
    ACS Catalysis2011 Article ASAP

    A new catalytic method for the synthesis of silyl enol ethers has been developed from the coupling reaction of ketones with CH2═CHSiMe3 by using a ruthenium hydride catalyst (PCy3)2(CO)RuHCl. The synthetic utility of silyl enol ethers was demonstrated for ...

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• 

  A Practical Protocol for the Highly E-Selective Formation of Aryl-Substituted Silylketene Acetals

  Wesley R. R. Harker, Emma L. Carswell and David R. Carbery
  Organic Letters2010 12 (16), 3712-3715

  • A Practical Protocol for the Highly E-Selective Formation of Aryl-Substituted Silylketene Acetals

    Wesley R. R. Harker, Emma L. Carswell and David R. Carbery
    Organic Letters2010 12 (16), 3712-3715

    The E/Z-selectivity in the formation of silylketene acetals derived from phenylacetate esters, mediated by LiHMDS, has been studied by in situ NMR techniques. The formation is seen to be highly E-selective with use of the newly developed protocol. ...

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• 

  Carbon Acid Induced Mukaiyama Aldol Type Reaction of Sterically Hindered Ketones

  Hikaru Yanai, Yasuhiro Yoshino, Arata Takahashi and Takeo Taguchi
  The Journal of Organic Chemistry2010 75 (15), 5375-5378

  • Carbon Acid Induced Mukaiyama Aldol Type Reaction of Sterically Hindered Ketones

    Hikaru Yanai, Yasuhiro Yoshino, Arata Takahashi and Takeo Taguchi
    The Journal of Organic Chemistry2010 75 (15), 5375-5378

    1,1,3,3-Tetrakis(trifluoromethanesulfonyl)propane (Tf2CHCH2CHTf2) is one of the most effective Brønsted acid precatalysts for the Mukaiyama aldol type reactions of sterically hindered ketones. By using Tf2CHCH2CHTf2 in a range from 0.5 to 2.0 mol %, the ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  N-Heterocyclic Carbene-Organocatalyzed Ring-Opening Polymerization of Ethylene Oxide in the Presence of Alcohols or Trimethylsilyl Nucleophiles as Chain Moderators for the Synthesis of α,ω-Heterodifunctionalized Poly(ethylene oxide)s

  Jean Raynaud, Christelle Absalon, Yves Gnanou and Daniel Taton
  Macromolecules2010 43 (6), 2814-2823

  • N-Heterocyclic Carbene-Organocatalyzed Ring-Opening Polymerization of Ethylene Oxide in the Presence of Alcohols or Trimethylsilyl Nucleophiles as Chain Moderators for the Synthesis of α,ω-Heterodifunctionalized Poly(ethylene oxide)s

    Jean Raynaud, Christelle Absalon, Yves Gnanou and Daniel Taton
    Macromolecules2010 43 (6), 2814-2823

    The present study describes innovations in the ring-opening polymerization (ROP) of ethylene oxide (EO) using N-heterocyclic carbenes (NHCs) as organocatalysts, which enables the synthesis of α,ω-heterodifunctionalized poly(ethylene oxide)s (PEOs). Two ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Group Transfer Polymerization of (Meth)acrylic Monomers Catalyzed by N-Heterocyclic Carbenes and Synthesis of All Acrylic Block Copolymers: Evidence for an Associative Mechanism

  Jean Raynaud, Yves Gnanou and Daniel Taton
  Macromolecules2009 42 (16), 5996-6005

  • Group Transfer Polymerization of (Meth)acrylic Monomers Catalyzed by N-Heterocyclic Carbenes and Synthesis of All Acrylic Block Copolymers: Evidence for an Associative Mechanism

    Jean Raynaud, Yves Gnanou and Daniel Taton
    Macromolecules2009 42 (16), 5996-6005

    N-Heterocyclic carbenes (NHCs), namely, 1,3-bis-(diisopropyl)imidazol-2-ylidene (1) and 1,3-bis(di-tert-butyl)imidazol-2-ylidene (2) were employed as neutral organocatalysts to bring about the group transfer polymerization (GTP) of both methacrylic and ...

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