Synthesis of New gamma-Lactams with gem-Difluorinated Side Chains

Ali Soulieman (1, 2) , Nicolas Gouault (1) , Thierry Roisnel (1) , Frédéric Justaud (1) , Joël Boustie (1) , René Grée (1) , Ali Hachem (2, 3)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LU / ULB - الجامعة اللبنانية [بيروت] = Lebanese University [Beirut] = Université libanaise [Beyrouth]
3 Agence universitaire de la Francophonie (Beyrouth, Lebanon)

A short and efficient approach has been designed for the synthesis of new gamma-lactams that feature gem -difluorinated side-chains in position 4. The key steps involve 1,4-addition of nitroalkane anions on electrophilic gem -difluoroalkenes, followed by a cascade nitro reduction-heterocyclization. This flexible strategy also allows easy introduction of substituents in positions 3 or 5.

Mots clés: fluorine; gamma lactams; gem-difluoropropargyl; heterocycles; synthesis

Domaines: Chimie

Ali Soulieman, Nicolas Gouault, Thierry Roisnel, Frédéric Justaud, Joël Boustie, et al.. Synthesis of New gamma-Lactams with gem-Difluorinated Side Chains. SYNLETT, 2019, 30 (20), pp.2258-2262. ⟨10.1055/s-0039-1690715⟩. ⟨hal-02438548⟩