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

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

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