Palladium-catalysed direct stereoselective synthesis of deoxyglycosides from glycals

Abhijit Sau, Ryan Williams, Carlos Palo Nieto, Antonio Franconetti Garcia, Sandra Medina Villar, Carmen Galan

Research output: Contribution to journalArticle (Academic Journal)peer-review

39 Citations (Scopus)
201 Downloads (Pure)

Abstract

Palladium (II) in combination with a monodentate phosphine ligand enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Initial mechanistic studies suggest that in the presence of N-phenyl-2-(di-tert-butylphosphino)pyrrole as the ligand, the reaction proceeds via an alkoxy-palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is exemplified with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.
Original languageEnglish
Pages (from-to)3640–3644
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number13
Early online date17 Feb 2017
DOIs
Publication statusPublished - 20 Mar 2017

Keywords

  • acetals
  • asymmetric catalysis
  • deoxyglycosides
  • glycosylation
  • palladium

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