Intramolecular hydroamination of difluoropropargyl amides: regioselective synthesis of fluorinated beta- and gamma-lactams.
Functionalized gem-difluoro beta- and gamma-lactams were synthesized through a novel intramolecular hydroamination reaction of difluoropropargyl amides. beta-Lactams were obtained via a Baldwin disfavored 4-exo-digonal cyclization using palladium acetate as the catalyst, whereas gamma-lactams were produced under basic conditions. Acid hydration of gamma-lactams produced ketoamides or hemiaminals selectively.
Fustero
Santos
S
Departamento de Química OrgAnica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
Fernández
Begoña
B
Bello
Paula
P
Pozo
Carlos Del
CD
Arimitsu
Satoru
S
Hammond
Gerald B
GB