N-heterocyclic carbene-catalyzed silyl enol ether formation

Org Lett. 2008 Mar 6;10(5):877-80. doi: 10.1021/ol703025b. Epub 2008 Jan 31.

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 degrees C in THF.

MeSH terms

  • Catalysis
  • Combinatorial Chemistry Techniques
  • Ethers / chemical synthesis*
  • Hydrocarbons / chemistry
  • Ketones / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Organosilicon Compounds / chemical synthesis*
  • Organosilicon Compounds / chemistry

Substances

  • Ethers
  • Hydrocarbons
  • Ketones
  • Organosilicon Compounds
  • carbene
  • Methane