1,2‐N‐Migration in a Gold‐Catalysed Synthesis of Functionalised Indenes by the 1,1‐Carboalkoxylation of Ynamides |
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| Authors: | Holly V Adcock Dr Thomas Langer Dr Paul W Davies |
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| Institution: | 1. School of Chemistry, University of Birmingham (UK), Fax: (+44)?121‐4144403;2. AstraZeneca, Pharmaceutical Development, Silk Road Business Park, Macclesfield, SK10 2NA (UK) |
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| Abstract: | 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. |
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| Keywords: | carbenes cycloisomerisation gold regioselectivity ynamides |
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