Sequential synthesis of (E)-alpha,beta-unsaturated primary amides with complete stereoselectivity.
A novel, efficient, and totally stereoselective synthesis of (E)-alpha,beta-unsaturated primary amides is reported. This process is consistent with a SmI(2)-mediated sequential reaction of an unmasked samarium chloroacetamide enolate with an aldehyde, followed by a beta-elimination to produce (E)-alpha,beta-unsaturated primary amides in good yields.
Concellón
José M
JM
Departamento de Química Organica e Inorgánica, Facultad de Química, Universidad de Oviedo, Spain. jmcg@uniovi.es
Rodríguez-Solla
Humberto
H
Concellón
Carmen
C
Simal
Carmen
C
Alvaredo
Noemí
N
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000577:Amides