Synthesis of Novel Cyclic Nitrones with gem‐Difluoroalkyl Side Chains Through Cascade Reactions,European Journal of Organic Chemistry

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Synthesis of Novel Cyclic Nitrones with gem‐Difluoroalkyl Side Chains Through Cascade Reactions
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2020-08-12 , DOI: 10.1002/ejoc.202000972
Ali Souleiman ₁ , Rima Ibrahim ₂ , Zeinab Barakat ₂ , Nicolas Gouault ₃ , Thierry Roisnel ₄ , Joel Boustie ₅ , Rene Gree ₆ , Ali Hachem ₇

Affiliation

New mono‐ and bicyclic nitrones containing a CF₂ group have been efficiently synthetized starting from propargylic fluorides. The key steps involve isomerization of propargylic alcohols to enones, followed by nucleophilic addition of nitro alkane anions and then intramolecular Michael additions. The last step is a reductive cyclisation from the nitro group.