Synthesis of sterically hindered enamides via a Ti-mediated condensation of amides with aldehydes and ketones.
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.
Novartis Institutes for Biomedical Research, Cambridge, MA 02139, USA.
Julien
J
Genovino
Bharat
B
Lagu
Yaping
Y
Wang
B Barry
BB
Touré
D000447:Aldehydes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D014025:Titanium / Q000737:chemistry
D000447:Aldehydes; D000577:Amides; D007659:Ketones; C025096:titanium tetrachloride; D014025:Titanium