Highly enantioselective [4 + 2] cyclization of chloroaldehydes and 1-azadienes catalyzed by N-heterocyclic carbenes

Chem Commun (Camb). 2012 Nov 14;48(88):10907-9. doi: 10.1039/c2cc35273g.

Abstract

Highly functionalized dihydropyridinones were synthesized via the N-heterocyclic carbene-catalyzed enantioselective [4 + 2] annulation of α-chloroaldehydes and azadienes. Hydrogenation of the resulted dihydropyridinones afforded the corresponding piperidinones with high enantiopurity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Aza Compounds / chemistry*
  • Cyclization
  • Hydrogenation
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Pyridones / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Aza Compounds
  • Pyridones
  • carbene
  • Methane