Tetrakis(trifluoromethanesulfonyl)propane: highly effective Brønsted acid catalyst for vinylogous Mukaiyama-Michael reaction of alpha,beta-enones with silyloxyfurans

Chem Commun (Camb). 2008 May 28:(20):2385-7. doi: 10.1039/b800815a. Epub 2008 Apr 8.

Abstract

1,1,3,3-Tetrakis(trifluoromethanesulfonyl)propane was found as an excellent Brønsted acid catalyst for the Mukaiyama-Michael reaction of alpha,beta-enones with 2-silyloxyfurans; using beta,beta-disubstituted enones as a Michael acceptor, an excellent yield construction of quaternary carbon centers could be achieved; in addition, very low catalyst loading of Brønsted acid was used in a range from 0.05 to 1.0 mol%.

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Furans / chemical synthesis
  • Furans / chemistry*
  • Ketones / chemical synthesis
  • Ketones / chemistry*
  • Mesylates / chemistry*
  • Propane / analogs & derivatives*
  • Propane / chemistry
  • Vinyl Compounds / chemical synthesis*
  • Vinyl Compounds / chemistry

Substances

  • Alkenes
  • Furans
  • Ketones
  • Mesylates
  • Vinyl Compounds
  • trifluoromethanesulfonic acid
  • Propane