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Divergent ynamide reactivity in the presence of azides - an experimental and computational study
Veronica Tona1, Stefan A Ruider1,2, Martin Berger1
1Institute of Organic ChemistryFaculty of Chemistry , University of Vienna , Währinger Straße 38 , 1090 Vienna , Austria .
Abstract:
An unusually divergent reactivity of ynamides in the presence of azides is reported. This new keteniminium-based methodology, which only requires triflic acid as promoter, facilitates access to β-enaminoamides and biologically important oxazolidine-2,4-diones in a highly selective, divergent manner that is fully controllable by the present azide. A mechanistic rationale for these divergent reaction pathways is delineated and supported by extensive density functional theory analyses, as well as selected mechanistic experiments.
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