C-Glycosyl Styrene Type Compounds by Pd-Catalyzed Cross-Coupling Reactions of Anhydro-Aldose Tosylhydrazones with Benzyl Bromides

Tímea Kaszás, Marietta Tóth, Peter Langer, László Somsák

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

C-Glycopyranosyl styrene type compounds are valuable synthetic intermediates whose syntheses are known in rather lengthy procedures. Herein palladium-catalyzed cross-couplings of O-peracylated 2,6-anhydro-aldose tosylhydrazones with benzyl bromides were studied under thermic conditions in the presence of LiOtBu. The reactions gave the corresponding C-glycopyranosyl styrenes in up to 59% yields. The transformations represent a new, short synthetic sequence to get this type of glycomimetic compounds in 4–5 steps from a free aldose. (Figure presented.).

Original languageEnglish
Pages (from-to)105-117
Number of pages13
JournalAdvanced Synthesis and Catalysis
Volume361
Issue number1
DOIs
Publication statusPublished - Jan 11 2019

Keywords

  • Alkenes
  • Anhydro-aldose tosylhydrazones
  • C-Glycosides
  • Carbenes
  • Carbohydrates
  • Cross-coupling
  • C−C coupling

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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