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 Bebbington

Research output: Contribution to journalArticleResearchpeer-review

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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Stereochemistry
Gold
propadiene
sulfamic acid

Keywords

  • Allenes
  • Gold catalysis
  • Hydroamination
  • Sulfamidates

Cite this

Higginbotham, Mari C.M. ; Kennedy, Lorna ; Lindsay, Anita G. ; Troester, Andreas ; Bebbington, Magnus. / Gold(I)-catalysed synthesis of cyclic sulfamidates : Current scope, stereochemistry and competing ene-allene cycloisomerisation. In: Tetrahedron. 2015 ; Vol. 71, No. 4. pp. 727-737.
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Gold(I)-catalysed synthesis of cyclic sulfamidates : Current scope, stereochemistry and competing ene-allene cycloisomerisation. / Higginbotham, Mari C.M.; Kennedy, Lorna; Lindsay, Anita G.; Troester, Andreas; Bebbington, Magnus.

In: Tetrahedron, Vol. 71, No. 4, 28.01.2015, p. 727-737.

Research output: Contribution to journalArticleResearchpeer-review

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