A novel base-induced isomerization gives access to unprecedented (E)-exo-glycals

Guillaume Eppe, Lidia Dumitrescu, Olivier Pierrot, Tianlei Li, Weidong Pan, Stéphane P. Vincent

Research output: Contribution to journalArticle

Abstract

Bump the base: This study reports the discovery of the base-induced Z-to-E isomerization of exo-glycals bearing an electron-withdrawing group (EWG). The scope of this novel transformation regarding the carbohydrate unit is also discussed. After elucidating the mechanism, preparation of novel (E)-exo- glycals was performed (TBS=tert-butyldimethylsilyl).

Original languageEnglish
Pages (from-to)11547-11552
Number of pages6
JournalChemistry: A European Journal
Volume19
Issue number35
DOIs
Publication statusPublished - 26 Aug 2013

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Keywords

  • carbohydrates
  • enol ethers
  • isomerization
  • phosphonates
  • stereochemistry

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