A novel base-induced isomerization gives access to unprecedented (E)-exo-glycals.
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).
['Eppe|Guillaume|G|', 'Dumitrescu|Lidia|L|', 'Pierrot|Olivier|O|', 'Li|Tianlei|T|', 'Pan|Weidong|W|', 'Vincent|Stéphane P|SP|']
D000468:Alkalies D002241:Carbohydrates D004987:Ethers D063065:Organophosphonates D013237:Stereoisomerism
isomerization carbohydrates enol ethers phosphonates stereochemistry