Perfluorophenylboronic acid-catalyzed direct α-stereoselective synthesis of 2-deoxygalactosides from deactivated peracetylated d-galactal

Madhu Babu Tatina, Ziad Moussa, Mengxin Xia, Zaher M.A. Judeh

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

Perfluorophenylboronic acid 1c catalyzes the direct stereoselective addition of alcohol nucleophiles to deactivated peracetylated d-galactal to give 2-deoxygalactosides in 55-88% yield with complete α-selectivity. The unprecedented results reported here also enable the synthesis of disaccharides containing the 2-deoxygalactose moiety directly from the deactivated peracetylated d-galactal. This convenient and metal-free glycosylation method works well with a wide range of alcohol nucleophiles as acceptors and tolerates a range of functional groups without the formation of the Ferrier byproduct and without the need for a large excess of nucleophiles or additives. The method is potentially useful for the synthesis of a variety of α-2-deoxygalactosides.

Original languageEnglish
Pages (from-to)12204-12207
Number of pages4
JournalChemical Communications
Volume55
Issue number81
DOIs
Publication statusPublished - 2019

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • General Chemistry
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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