title: Tertiary amines as synthetic equivalents of vinyl cations: zinc bromide promoted coupling of propargylamines with α-isocyanoacetamides to give 2,4,5-trisubstituted oxazoles initiated by an internal redox process.
abstract: Crabée interrupted: Propargylamines 1 react with α-isocyanoacetamides 2 in the presence of zinc bromide to afford vinyl oxazoles 3. The transformation, wherein the propargylamine acts as a vinyl cation synthetic equivalent, involves a domino sequence incorporating a 1,5-hydride shift, intermolecular trapping/cyclization, and a 1,6-elimination (see scheme).
authors.forename: Yann
authors.initials: Y
authors.lastname: Odabachian
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu