The tandem Heck-allylic substitution reaction: a novel route to lactams.
[reaction: see text] A novel route to substituted lactams has been developed using a tandem Heck-allylic substitution reaction. The palladium-catalyzed reaction between omega-olefinic N-tosyl amides and vinylic bromides affords in one step the substituted pyrrolidones and piperidones in 49-82% isolated yield. In addition, it is shown that an N-phenyl amide can act as a nucleophile in intramolecular allylic substitution reactions.
Pinho
Pedro
P
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Minnaard
Adriaan J
AJ
Feringa
Ben L
BL
D002384:Catalysis; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium
D007769:Lactams; D010165:Palladium