Stereoselective glycosylation reactions with chiral auxiliaries

Jin Hwan Kim, Hai Yang, Geert Jan Boons*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

Good neighbors: A chiral auxiliary is used for the first time to control the anomeric selectivity of glycosylation reactions. In this approach, upon treatment with an activator A+, neighboring-group participation pation of an (S)-ethoxycarbonylbenzyl auxiliary at C2 leads to the formation of 1,2-cis glycosides, probably via a transfused ethyloxonium ion intermediate (see scheme).

Original languageEnglish
Pages (from-to)947-949
Number of pages3
JournalAngewandte Chemie - International Edition
Volume44
Issue number6
DOIs
Publication statusPublished - 2 Feb 2005
Externally publishedYes

Keywords

  • Anomeric control
  • Carbohydrates
  • Chiral auxiliaries
  • Glycosides
  • Glycosylation

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