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


Published in:
Chemistry - A European Journal, 19, 37, 12229-12233
Year:
2013
Publisher:
Weinheim, Wiley-Blackwell
ISSN:
0947-6539
Keywords:
Laboratories:




 Record created 2013-09-14, last modified 2018-09-13


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