1,4-Addition of silicon dienoates to α,β-unsaturated aldehydes catalyzed by in situ-generated silicon Lewis acid

Chem Commun (Camb). 2010 Dec 14;46(46):8728-30. doi: 10.1039/c0cc02438d. Epub 2010 Oct 22.

Abstract

In situ-generated silyl methide species (R(3)Si-CTf(2)R') effectively catalyzed the reaction of β-substituted α,β-unsaturated aldehydes with silicon dienoates such as 3-bromo-2-TESO-furan to give the corresponding γ-adducts with excellent 1,4-selectivity and good anti selectivity.

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Molecular Structure
  • Organosilicon Compounds / chemical synthesis*
  • Organosilicon Compounds / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Organosilicon Compounds