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
Odabachian, Yann; Wang, Qian; Zhu, Jieping
2013

Abstract

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

Details

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
Author(s) Odabachian, Yann ; Wang, Qian ; Zhu, Jieping
Published in Chemistry - A European Journal
Pagination 5
Volume 19
Issue 37
Pages 12229-12233
Date 2013
Publisher Weinheim, Wiley-Blackwell
ISSN 0947-6539
Keywords
DOI https://doi.org/10.1002/chem.201302106
Other identifier(s) View record in Web of Science
Laboratories LSPN
Record Appears in Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date 2013-09-14

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