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

doi:10.1002/chem.201300969

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

Chemistry. 2013 Aug 26;19(35):11547-52. doi: 10.1002/chem.201300969. Epub 2013 Jul 25.

Authors

Guillaume Eppe¹, Lidia Dumitrescu, Olivier Pierrot, Tianlei Li, Weidong Pan, Stéphane P Vincent

Affiliation

¹ University of Namur (UNamur), Département de Chimie, Laboratoire de Chimie Bio-Organique, rue de Bruxelles 61, 5000 Namur, Belgium.

PMID: 23893767
DOI: 10.1002/chem.201300969

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).

Keywords: carbohydrates; enol ethers; isomerization; phosphonates; stereochemistry.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkalies / chemistry*
Carbohydrates / chemistry*
Ethers / chemistry*
Organophosphonates / chemistry*
Stereoisomerism

Substances

Alkalies
Carbohydrates
Ethers
Organophosphonates