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Updated: Jan 24, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Site-Selective Debenzylation of C-Allyl Iminosugars Enables Their Stereocontroled Structure Diversification at the
Quentin Foucart1, Jérôme Marrot2, Jérôme Désiré1
1Université de Poitiers , IC2MP , UMR CNRS 7285, Equipe "Synthèse Organique", Groupe Glycochimie, 4 rue Michel Brunet , Poitiers 86073 Cedex 9 , France.
Abstract:
A C-2 regioselective debenzylative cycloetherification/reductive elimination sequence applied to perbenzylated C-allyl iminosugars is described. This NIS/TMSOTf-triggered deprotection was successfully applied to five-, six-, and seven-membered C-allyl iminosugars including 1,2 cis and 1,2 trans stereoisomers. It allows rapid introduction of structural diversity at the key C-2 position in a stereoselective manner exploiting the anchimeric assistance of the intracyclic N-benzyl group, giving access to the 2-acetamido and 2-fluoro d-gluco configured C-allyl iminosugars and to the epimeric d-manno derivative.
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