N-heterocyclic carbene-catalyzed Mukaiyama aldol reactions

Org Lett. 2007 Mar 15;9(6):1013-6. doi: 10.1021/ol0630494. Epub 2007 Feb 13.

Abstract

N-Heterocyclic carbenes were shown to be highly effective catalysts to promote Mukaiyama aldol reactions. In the presence of only 0.5 mol % of N-heterocyclic carbene (5), various aldehydes and 2,2,2-trifluoroacetophenone underwent Mukaiyama aldol reactions in THF with trimethylsilyl ketene acetal (2) at 23 degrees C as well as with trimethylsilyl enol ether (7) at 0 degrees C to afford aldol adducts in good yields. These conditions are extremely mild and operationally simple and tolerate various functional groups. [reaction: see text]

MeSH terms

  • Acetophenones / chemistry
  • Aldehydes / chemistry*
  • Catalysis
  • Ethers / chemistry
  • Hydrocarbons / chemistry
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Models, Chemical
  • Stereoisomerism
  • Temperature
  • Trimethylsilyl Compounds / chemistry*

Substances

  • Acetophenones
  • Aldehydes
  • Ethers
  • Hydrocarbons
  • Trimethylsilyl Compounds
  • carbene
  • 3-hydroxybutanal
  • Methane