Reaction of N-vinylic phosphazenes with alpha,beta-unsaturated aldehydes. Azatriene-mediated synthesis of dihydropyridines and pyridines derived from beta-amino acids

J Org Chem. 2006 Aug 4;71(16):6020-30. doi: 10.1021/jo060775b.

Abstract

Aza-Wittig reaction of N-vinylic phosphazenes (1,2 addition), derived from diphenylmethylphosphine or derived from trimethylphosphine with alpha,beta-unsaturated aldehydes, leads to the formation of 3-azatrienes through a [2 + 2]-cycloaddition-cycloreversion sequence. The presence of an alkyl substituent in position 3 of N-vinylic phosphazenes increases the steric interactions, and [4 + 2] periselectivity (1,4 addition) is observed. Reaction of azatrienes with alpha,beta-unsaturated aldehydes yields pyridines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Amino Acids / chemistry*
  • Aza Compounds / chemistry*
  • Computer Simulation
  • Cyclization
  • Dihydropyridines / chemical synthesis*
  • Dihydropyridines / chemistry
  • Models, Molecular
  • Molecular Structure
  • Phosphoranes / chemistry*
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Static Electricity

Substances

  • Aldehydes
  • Amino Acids
  • Aza Compounds
  • Dihydropyridines
  • Phosphoranes
  • Pyridines