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Highly stereoselective synthesis of C-vinyl pyranosides via a Pd-mediated cycloetherification of 1-acetoxy-2,3-dideoxy-oct-2-enitols

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Identifiers
DOI: 10.1016/j.carres.2014.07.002
Keywords
  • C-Glycosides
  • C-Vinyl Pyranosides
  • 1
  • 2-Dideoxy-Hept-1-Enitols
  • 2
  • 3-Dideoxy-Oct-2-Enitols
  • Cycloetherification
  • Pd-Mediated
  • Dach Ligands
Disciplines
  • Chemistry

Abstract

Abstract Oct-2-enitols undergo a Pd0-mediated cyclization to produce C-vinyl α-gluco- and α-galactopyranosides, and C-vinyl β-mannopyranoside in good yield and with high stereoselectivity. While substrate control demonstrates a clear stereochemical preference during cyclization, the α- and β-epimeric ratios are enhanced by double diastereoselection using the (S,S) or (R,R)-DACH ligands.

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