Gold(I)-catalysed synthesis of cyclic sulfamidates : current scope, stereochemistry and competing ene-allene cycloisomerisation

Mari Higginbotham, Lorna Kennedy, Anita Lindsay, Andreas Troester, Magnus William Paul Bebbington

Research output: Contribution to journalArticle

4 Citations (Scopus)
218 Downloads (Pure)

Abstract

Six-membered cyclic sulfamidates are prepared in high yields by treatment of allenic sulfamates with readily available Ph3PAuNTf2. The reaction enables formation of N-substituted quaternary centres in high yields. The relative stereochemistry has been unambiguously determined. A π-rearrangement is faster than hydroamination in the case of an allyl-substituted sulfamate and a mechanism is proposed for this process.
Original languageEnglish
Pages (from-to)727-737
Number of pages11
JournalTetrahedron
Volume71
Issue number4
Early online date5 Dec 2014
DOIs
Publication statusPublished - 28 Jan 2015

Keywords

  • gold catalysis
  • hydroamination
  • allenes
  • sulfamidates

ASJC Scopus subject areas

  • Chemistry(all)

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