Modified Julia Olefination on Sugar-Derived Lactones: Synthesis of Difluoro- exo -glycals

Samuel Habib (1) , David Gueyrard (1)

1 CO2GLYCO - Chimie Organique 2-Glycochimie

We report the preparation of difluoro-exo-glycals by gem-difluoroolefination of benzylated sugar-derived lactones using a modified Julia reaction. The addition is highly stereoselective, and the Smiles-rearrangement–elimination sequence can be carried out under microwave irradiation.

Keywords: Lactones, Olefination, Fluorine, Carbohydrates, Glycals

Domains: Organic chemistry

Samuel Habib, David Gueyrard. Modified Julia Olefination on Sugar-Derived Lactones: Synthesis of Difluoro- exo -glycals. European Journal of Organic Chemistry, 2015, 2015 (4), pp.871-875. ⟨10.1002/ejoc.201403175⟩. ⟨hal-02123915⟩