research article
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
Crabe interrupted: Propargylamines 1 react with a-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
Type
research article
Web of Science ID
WOS:000323731200012
Author(s)
Date Issued
2013
Publisher
Published in
Volume
19
Issue
37
Start page
12229
End page
12233
Subjects
Editorial or Peer reviewed
REVIEWED
Written at
EPFL
EPFL units
Available on Infoscience
September 14, 2013
Use this identifier to reference this record