Title

A Novel Base-Induced Isomerization Gives Access to Unprecedented ( E)- exo-Glycals.

Authors

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

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).

Subjects

ISOMERIZATION; GLYCALS; DIASTEREOISOMERS; PROTECTIVE groups (Chemistry); NUCLEAR magnetic resonance spectroscopy

Publication

Chemistry - A European Journal, 2013, Vol 19, Issue 35, p11547

ISSN

0947-6539

Publication type

Academic Journal

DOI

10.1002/chem.201300969