Gold-catalysed cycloisomerisation of ynamides to access 2,2-disubstituted tetrahydrothiophene motifs

Parmjit Heer, Paul Davies

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Abstract

Ynamides bearing a tethered allyl sulfoxide undergo a gold-catalysed cycloisomerisation to afford 2-carboxylic amide tetrahydrothiophenes and their benzofused analogues. The reactions are initiated by a formal 7-endo-dig cyclisation and accommodate a range of different substituents. The use of N-allyl ynamides provided a route into novel spirocyclic ε-lactam structures.
Original languageEnglish
Pages (from-to)1-4
JournalSynlett
Volume2021
Issue number00
Early online date13 Mar 2021
DOIs
Publication statusE-pub ahead of print - 13 Mar 2021

Bibliographical note

Funding Information: We thank the EPSRC for funding (EP/F031254/1).

Keywords

  • gold
  • isomerization
  • regioselectivity
  • thiophenecarboxamides
  • ylides
  • ynamides

ASJC Scopus subject areas

  • Organic Chemistry

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