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Issue 9, 2016
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Divergent ynamide reactivity in the presence of azides – an experimental and computational study

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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.

Graphical abstract: Divergent ynamide reactivity in the presence of azides – an experimental and computational study

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Publication details

The article was received on 03 May 2016, accepted on 24 May 2016 and first published on 10 Jun 2016


Article type: Edge Article
DOI: 10.1039/C6SC01945E
Citation: Chem. Sci., 2016,7, 6032-6040
  • Open access: Creative Commons BY license
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    Divergent ynamide reactivity in the presence of azides – an experimental and computational study

    V. Tona, S. A. Ruider, M. Berger, S. Shaaban, M. Padmanaban, L. Xie, L. González and N. Maulide, Chem. Sci., 2016, 7, 6032
    DOI: 10.1039/C6SC01945E

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