Synthesis of thiomorpholin‐3‐ones by a gold‐catalysed oxidative cyclisation‐rearrangement cascade from ynamides

Thomas Baker, Paul Davies

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)
125 Downloads (Pure)

Abstract

A gold‐catalyzed oxidative N‐cyclisation strategy allows for the preparation of α‐aryl thiomorpholin‐3‐ones from readily assembled ynamides bearing tethered thioethers. A cascade of oxidation, cyclisation and then [2,3]‐ or [1,2]‐sigmatropic rearrangement of the resulting sulfonium ylide proceeds under mild reaction conditions. Cyclisation and intermolecular oxidation are in competition at two different stages of the reaction. The required switch in selectivity between these processes can be managed by combining pyridine N‐oxide oxidant with an IPrAuCl‐derived catalyst.
Original languageEnglish
Pages (from-to)5201-5204
Number of pages4
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number31-32
Early online date24 Jun 2019
DOIs
Publication statusPublished - 19 Aug 2019

Keywords

  • Cyclisation
  • Gold
  • Nitrogen heterocycles
  • Oxidation
  • Ynamide

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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