1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides

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  • AstraZeneca R&D


Unique α-hemiaminal ether gold carbene intermediates were accessed by a gold-catalysed 1,1-carboalkoxylation strategy and evolved through a highly selective 1,2-N-migration. This skeletal rearrangement gave functionalised indenes, and isotopic labelling confirmed the rare C-N bond cleavage of the ynamide moiety. The effect of substituents on the migration has been explored, and a model is proposed to rationalise the observed selectivity.


Original languageEnglish
Pages (from-to)7262-7266
Number of pages5
JournalChemistry: A European Journal
Issue number24
Early online date14 May 2014
Publication statusPublished - 10 Jun 2014


  • carbenes, cycloisomerisation, gold, regioselectivity, ynamides

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