title: A novel base-induced isomerization gives access to unprecedented (E)-exo-glycals.
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).
authors.affiliation: University of Namur (UNamur), Département de Chimie, Laboratoire de Chimie Bio-Organique, rue de Bruxelles 61, 5000 Namur, Belgium.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Eppe
authors.forename: Lidia
authors.initials: L
authors.lastname: Dumitrescu
authors.forename: Olivier
authors.initials: O
authors.lastname: Pierrot
authors.forename: Tianlei
authors.initials: T
authors.lastname: Li
authors.forename: Weidong
authors.initials: W
authors.lastname: Pan
authors.forename: Stéphane P
authors.initials: SP
authors.lastname: Vincent
mesh_terms: D000468:Alkalies / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000468:Alkalies; D002241:Carbohydrates; D004987:Ethers; D063065:Organophosphonates
keywords: carbohydrates; enol ethers; isomerization; phosphonates; stereochemistry