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

Mari C.M. Higginbotham, Lorna Kennedy, Anita G. Lindsay, Andreas Troester, Magnus W.P. Bebbington

Research output: Contribution to journalArticle

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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
DOIs
StatePublished - 28 Jan 2015

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Keywords

  • Allenes
  • Gold catalysis
  • Hydroamination
  • Sulfamidates

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