Pd-catalyzed coupling reactions of anhydro-aldose tosylhydrazones with aryl bromides to produce substituted exo-glycals

Tímea Kaszás, Anton Ivanov, Marietta Tóth, Peter Ehlers, Peter Langer, László Somsák

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Palladium-catalyzed cross-couplings of O-peracylated and O-permethylated 2,6-anhydro-aldose tosylhydrazones with aryl halides were studied under thermic conditions in the presence of LiOtBu and phosphine ligands. The reactions gave the corresponding aryl substituted exo-glycals as mixtures of diastereomers in 11–75% yields. The transformations represent a new access to these types of glycomimetic compounds. The double bond of some aryl substituted exo-glycals was saturated to give good yields of benzylic C-glycosyl derivatives.

Original languageEnglish
Pages (from-to)30-38
Number of pages9
JournalCarbohydrate Research
Volume466
DOIs
Publication statusPublished - Aug 2018

    Fingerprint

Keywords

  • Anhydro-aldose tosylhydrazones
  • Carbenes
  • Cross coupling
  • Pd-catalysis
  • Substituted exo-glycals

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this