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

Holly V. Adcock, Thomas Langer, Paul W. Davies*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

48 Citations (Scopus)
167 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)7262-7266
Number of pages5
JournalChemistry: A European Journal
Volume20
Issue number24
Early online date14 May 2014
DOIs
Publication statusPublished - 10 Jun 2014

Keywords

  • carbenes
  • cycloisomerisation
  • gold
  • regioselectivity
  • ynamides

ASJC Scopus subject areas

  • Chemistry(all)

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