Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 24, Pages 7262-7266Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201403040
Keywords
carbenes; cycloisomerisation; gold; regioselectivity; ynamides
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Funding
- EPSRC
- AstraZeneca plc
- Engineering and Physical Sciences Research Council [970746] Funding Source: researchfish
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Unique alpha-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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