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A Novel Base‐Induced Isomerization Gives Access to Unprecedented ( E )‐ exo ‐Glycals
Author(s) -
Eppe Guillaume,
Dumitrescu Lidia,
Pierrot Olivier,
Li Tianlei,
Pan Weidong,
Vincent Stéphane P.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300969
Subject(s) - isomerization , scope (computer science) , computer science , chemistry , service (business) , base (topology) , mechanism (biology) , world wide web , combinatorial chemistry , information retrieval , stereochemistry , organic chemistry , catalysis , business , mathematics , philosophy , epistemology , mathematical analysis , marketing , programming language
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).