A Novel Base‐Induced Isomerization Gives Access to Unprecedented (E)‐exo‐Glycals. Issue 35 (25th July 2013)

• Record Type: Journal Article
• Authors: Eppe, Guillaume; Dumitrescu, Lidia; Pierrot, Olivier; Li, Tianlei; Pan, Weidong; Vincent, Stéphane P.
• Is Part Of: Chemistry. Volume 19:Issue 35(2013)
• Page Start: 11547
• Page End: 11552
• Publication Date: 2013-07-25
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201300969
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Bump the base</bold>: This study reports the discovery of the base‐induced <italic>Z</italic>‐to‐<italic>E</italic> isomerization of <italic>exo</italic>‐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 (<italic>E</italic>)‐<italic>exo</italic>‐ glycals was performed (TBS=<italic>tert</italic>‐butyldimethylsilyl).<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg36r46xr6" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>