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Divergent ynamide reactivity in the presence of azides - an experimental and computational study.

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 ?-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.

SUBMITTER: Tona V

PROVIDER: S-EPMC6022194 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

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Divergent ynamide reactivity in the presence of azides - an experimental and computational study.

Tona Veronica V Ruider Stefan A SA Berger Martin M Shaaban Saad S Padmanaban Mohan M Xie Lan-Gui LG González Leticia L Maulide Nuno N

Chemical science 20160610 9

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 s ...[more]

PMID: 30034744

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