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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
Authors
Publication date
2013
Publisher
Published in
Volume
19
Issue
37
Start page
12229
End page
12233
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
September 14, 2013
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