Silver-catalyzed transformation of propargylic amine N-oxides to enones and acyloxy ketones via isoxazolinium intermediates

Jian Fang Cui, Karen Ka Yan Kung, Hok Ming Ko, Tsz Wai Hui, Man Kin Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

8 Citations (Scopus)

Abstract

KGaA, Weinheim. A novel silver-catalyzed transformation of propargylic amine N-oxides with switchable product profiles has been developed. A diversity of enones with excellent E/Z ratios (up to >20:1) were obtained when the reactions were conducted in aprotic solvents. In contrast, 3-chlorobenzoxymethyl ketones and α-(3-chloro)-benzoxy enones were obtained by using protic solvents. Mechanistic studies suggested that in situ generated isoxazolinium ions are the key intermediates involved in these novel silver-catalyzed reaction pathways. Applications on the chemoselective modification of cysteine-containing peptides in aqueous medium have also been achieved.
Original languageEnglish
Pages (from-to)2965-2973
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number14-15
DOIs
Publication statusPublished - 1 Oct 2014

Keywords

  • Isoxazolinium salts
  • N-oxides
  • Peptide modification
  • Propargylic amines
  • Silver catalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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