A Novel Base‐Induced Isomerization Gives Access to Unprecedented (<i>E</i>)‐<i>exo</i>‐Glycals

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

Chemistry - A European Journal · 2013 · 11 citations · 52 references

Concepts

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). As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

References

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