Synthesis of sterically hindered enamides via a Ti-mediated condensation of amides with aldehydes and ketones

Chem Commun (Camb). 2012 Jul 7;48(53):6735-7. doi: 10.1039/c2cc32538a. Epub 2012 May 29.

Abstract

The first TiCl(4)-mediated condensation of secondary amides with aldehydes and ketones has been achieved. The reaction proceeds at room temperature and is complete within 5 h in most cases. The optimized procedure used 5 equiv of an amine base hinting that the in situ activation of both the amide and the Lewis acid is required. The reaction affords polysubstituted (E)-enamides.

MeSH terms

  • Aldehydes / chemistry*
  • Amides / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Titanium / chemistry

Substances

  • Aldehydes
  • Amides
  • Ketones
  • titanium tetrachloride
  • Titanium