Stereoelectronic effects determine oxacarbenium vs β-sulfonium ion mediated glycosylations

Thomas J Boltje, Jin-Hwan Kim, Jin Park, Geert-Jan Boons

Research output: Contribution to journalArticleAcademicpeer-review


Activation of a glycosyl donor protected with a 2-O-(S)-(phenylthiomethyl)benzyl ether chiral auxiliary results in the formation of an anomeric β-sulfonium ion, which can be displaced with sugar alcohols to give corresponding α-glycosides. Sufficient deactivation of such glycosyl donors by electron-withdrawing protecting groups is, however, critical to avoid glycosylation of an oxacarbenium ion intermediate. The latter type of glycosylation pathway can also be suppressed by installing additional substituents in the chiral auxiliary.

Original languageEnglish
Pages (from-to)284-7
Number of pages4
JournalOrganic Letters
Issue number2
Publication statusPublished - 21 Jan 2011
Externally publishedYes


  • Glycosides
  • Glycosylation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism
  • Sulfonium Compounds


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