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The synthesis of densely functionalised α-acyloxy enaminals and enaminones via a novel homogeneous silver(I) catalysed rearrangement

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Abstract

A synthesis of densely functionalised α-acyloxy enaminals and enaminones via a novel homogeneous silver(I) catalyzed rearrangement of 1-acyloxy-3-azido ketones is reported. This silver catalyzed reaction involves an internal redox process comprised of four net transformations: loss of nitrogen, reductive cleavage of the azide, 1,2-acyl migration and oxidation of the acyloxy position to an aldehyde (enaminal) or ketone (enaminone). These mild reaction conditions have been applied to acyclic, cyclic, and chiral substrates yielding the rearranged enaminals or enaminones in up to 91% yield, all of which prove to be stable, isolatable products.

Graphical abstract: The synthesis of densely functionalised α-acyloxy enaminals and enaminones via a novel homogeneous silver(i) catalysed rearrangement

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Publication details

The article was received on 19 Jul 2019, accepted on 14 Aug 2019 and first published on 15 Aug 2019


Article type: Communication
DOI: 10.1039/C9CC05614A
Chem. Commun., 2019, Advance Article

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    The synthesis of densely functionalised α-acyloxy enaminals and enaminones via a novel homogeneous silver(I) catalysed rearrangement

    K. Keskar, C. Zepeda-Velazquez, C. B. Dokuburra, H. A. Jenkins and J. McNulty, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC05614A

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