Palladium-catalyzed intramolecular cyanoamidation of alkynyl and alkenyl cyanoformamides.
[reaction: see text] The five- to seven-membered alpha-alkylidene lactams were prepared in 45-99% yield by the palladium-catalyzed cyanoamidation of alkynyl cyanoformamides. The reaction proceeded exclusively in a 5-exo mode, giving the corresponding (Z)-alkenes as major products. The reaction was also applied to 1,1-disubstituted alkenes to afford oxindoles bearing a quaternary carbon center.
Kobayashi
Yusuke
Y
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Japan.
Kamisaki
Haruhi
H
Yanada
Reiko
R
Takemoto
Yoshiji
Y
D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007769:Lactams / Q000138:chemical synthesis*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D000480:Alkynes; D000577:Amides; D007769:Lactams; D009570:Nitriles; D010165:Palladium