PPh3·HBr-DMSO mediated expedient synthesis of γ-substituted β,γ-unsaturated α-ketomethylthioesters and α-bromo enals: Application to the synthesis of 2-methylsulfanyl-3(2 H)-furanones

Kanchan Mal, Abhinandan Sharma, Prakas R. Maulik, Indrajit Das

Research output: Contribution to journalArticlepeer-review

54 Scopus citations

Abstract

An efficient chemoselective general procedure for the synthesis of γ-substituted β,γ-unsaturated α-ketomethylthioesters from α,β-unsaturated ketones has been achieved through an unprecedented PPh3·HBr-DMSO mediated oxidative bromination and Kornblum oxidation sequence. The newly developed reagent system serves admirably for the synthesis of α-bromoenals from enals. Furthermore, AuCl 3-catalyzed efficient access to 3(2H)-furanones from the above intermediates under extremely mild conditions are described.

Original languageEnglish
Pages (from-to)662-667
Number of pages6
JournalChemistry - A European Journal
Volume20
Issue number3
DOIs
StatePublished - 13 Jan 2014
Externally publishedYes

Keywords

  • chemoselectivity
  • cyclization
  • gold
  • oxidative bromination
  • triphenylphosphine hydrobromide

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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