N-heterocyclic carbene catalyzed reactions of α-bromo-α,β-unsaturated aldehydes/α,β-dibromoaldehydes with 1,3-dinucleophilic reagents

Chemistry. 2012 Feb 13;18(7):1914-7. doi: 10.1002/chem.201103358. Epub 2012 Jan 19.

Abstract

Carbenes ring true: N-Heterocyclic carbene (NHC) catalyzed reactions of α-bromo-α,β-unsaturated aldehydes/α,β-dibromoaldehydes with 1,3-dinucleophilic reagents, such as 1,3-dicarbonyl compounds, β-enamino ketones, and β-enamino esters through umpolung processes gave functionalized 3,4-dihydropyranones and 3,4-dihydropyridinones. The availability of the starting materials, lack of external oxidant, and usefulness of the products make this strategy attractive.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Esters
  • Hydrocarbons, Brominated / chemistry*
  • Indicators and Reagents
  • Ketones / chemical synthesis
  • Ketones / chemistry
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Aldehydes
  • Esters
  • Hydrocarbons, Brominated
  • Indicators and Reagents
  • Ketones
  • carbene
  • Methane