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Issue 91, 2018
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Intramolecular cycloaddition/rearrangement cascade from gold(III)-catalysed reactions of propargyl aryldiazoesters with cinnamyl imines

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Abstract

Conjugated cycloheptene-1,4-dione-enamines are cycloaddition products from a surprising rearrangement in a Au(III)-catalysed reaction between propargyl aryldiazoacetates and cinnamyl imines. This complex transformation occurs through an initial rapid Au(III)-catalysed [4+3]-cycloaddition to form dihydroazepinyl aryldiazoacetates followed by a subsequent uncatalyzed domino transformation that occurs by sequential [3+2]-cycloaddition-/nitrogen extrusion and acyloxy migration/retro-Michael addition/tautomerization.

Graphical abstract: Intramolecular cycloaddition/rearrangement cascade from gold(iii)-catalysed reactions of propargyl aryldiazoesters with cinnamyl imines

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Publication details

The article was received on 02 Oct 2018, accepted on 17 Oct 2018 and first published on 19 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC07885H
Citation: Chem. Commun., 2018,54, 12828-12831
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    Intramolecular cycloaddition/rearrangement cascade from gold(III)-catalysed reactions of propargyl aryldiazoesters with cinnamyl imines

    H. Qiu, H. Arman, W. Hu and M. P. Doyle, Chem. Commun., 2018, 54, 12828
    DOI: 10.1039/C8CC07885H

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