Diastereoselective sulfur ylide rearrangements from gold catalysed oxidation of ynamides

Joshua Priest, Louise Male, Paul Davies

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Abstract

The [2,3]-sigmatropic rearrangement of sulfonium ylides bearing substituted allyl groups creates two contiguous stereocentres. Low diastereoselectivity is typically observed from commonly used α-diazocarboxylic ester precursors. High diastereoselectivity was previously revealed in a gold-catalyzed multicomponent route into allyl sulfonium ylides by reaction of ynamide, oxidant and allyl sulfides. The effect of substrate modifications on the diastereoselectivity have been studied, with N-phenyl methanesulfonamide derived ynamides proving the most effective. This report includes an enhanced experimental procedure, and a demonstration that the gold-catalyzed process remains highly effective at −78 °C.
Original languageEnglish
Article number131757
JournalTetrahedron
Volume78
Early online date13 Nov 2020
DOIs
Publication statusPublished - 8 Jan 2021

Keywords

  • Sulfur ylide
  • Rearrangement
  • Gold carbenoid
  • Oxidation
  • Ynamide

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