Stereoselective oxindole synthesis by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with amides.
A new cyclization reaction occurred on treatment of 2-(alkynyl)aryl isocyanates with amides in the presence of a palladium(0)/diphosphine catalyst to stereoselectively form 3-(amidoalkylidene)oxindoles. A carbon-nitrogen bond as well as a carbon-carbon bond were simultaneously introduced onto the alkyne moiety to construct an oxindole skeleton with stereoselective placement of the amino substituent cis to the carbonyl group.
Miura
Tomoya
T
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Toyoshima
Takeharu
T
Takahashi
Yusuke
Y
Murakami
Masahiro
M