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

Research output: Contribution to journalArticlepeer-review

Authors

Colleges, School and Institutes

External organisations

  • AstraZeneca R&D
  • School of Chemistry; University of Birmingham; Edgbaston Birmingham B15 2TT UK

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.

Details

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

Keywords

  • carbenes, cycloisomerisation, gold, regioselectivity, ynamides

ASJC Scopus subject areas