title: Cu-catalyzed skeletal rearrangement of O-propargylic electron-rich arylaldoximes into amidodienes.
abstract: O-Propargylic oximes that possess an electron-rich p-(dimethylamino)phenyl group at the oxime moiety and an alkyl group at the propargylic position were efficiently converted in the presence of Cu(I) catalysts to the corresponding 1-amidodienes in good to excellent yields. The reaction proceeded via a 2,3-rearrangement, followed by isomerization of the resulting N-allenylnitrone to the amide, presumably through the oxaziridine intermediate.
authors.affiliation: Research and Analytical Center for Giant Molecules and ‡Department of Chemistry, Graduate School of Science, Tohoku University , Sendai 980-8578, Japan.
authors.forename: Itaru
authors.initials: I
authors.lastname: Nakamura
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Ishida
authors.forename: Masahiro
authors.initials: M
authors.lastname: Terada