A study of the conjugate addition of thionucleophiles to 2(5H)-furanones

Felix Busqué, Pedro De March, Marta Figueredo, Josep Font, Lluïsa González

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26 Citations (Scopus)

Abstract

Several new 4-thio-4,5-dihydro-2(3H)-furanones were prepared by the conjugate addition reactions of different thioacids, dithioacids, xanthates and dithiocarbamates to 2(5H)-furanones. When 5-methyl-2(5H)-furanone was used as the electrophilic substrate, the reaction was diastereoselective affording exclusively the cis-α,β-disubstituted butanolides. Some adducts were selectively hydrolysed to deliver a free thiol functionality. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Original languageEnglish
Pages (from-to)1492-1499
JournalEuropean Journal of Organic Chemistry
Issue number7
DOIs
Publication statusPublished - 26 Mar 2004

Keywords

  • Furanones
  • Lactones
  • Michael addition
  • Nucleophiles
  • Sulfur

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