Synthesis of Novel Cyclic Nitrones withgem-Difluoroalkyl Side Chains Through Cascade Reactions

Ali Soulieman (1, 2) , Rima Ibrahim (2) , Zeinab Barakat (2) , Nicolas Gouault (1) , Thierry Roisnel (1) , Joël Boustie (1) , René Grée (1) , Ali Hachem (2)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LU / ULB - الجامعة اللبنانية [بيروت] = Lebanese University [Beirut] = Université libanaise [Beyrouth]

New five-membered cyclic nitrones withgem-difluoroalkyl groups in gamma-position have been prepared by a 3-step sequence starting from propargylic alcohols. This domino process involves a base-mediated isomerization reaction to enones, which are trapped in situ by nitroalkane anions. In a final step, starting from these key precursors, a reduction-cyclization process affords the target molecules. Mono- and bicyclic nitrones have been prepared by this route which allows, as well, the synthesis of nitrones with functional groups in terminal position of the side chain.

Mots clés: Fluorine; Nitrones; Cascade reactions; Propargylic fluorides; Nitroalkanes

Domaines: Chimie; Chimie organique

Ali Soulieman, Rima Ibrahim, Zeinab Barakat, Nicolas Gouault, Thierry Roisnel, et al.. Synthesis of Novel Cyclic Nitrones withgem-Difluoroalkyl Side Chains Through Cascade Reactions. European Journal of Organic Chemistry, 2020, 2020 (35), pp.5741-5751. ⟨10.1002/ejoc.202000972⟩. ⟨hal-02957740⟩