First efficient synthesis of SF 5 -substituted pyrrolidines using 1,3-dipolar cycloaddition of azomethine ylides with pentafluorosulfanyl-substituted acrylic esters and amides

Ewelina Falkowska (1) , Vincent Tognetti (1) , Laurent Joubert (1) , Philippe Jubault (1) , J.-P. Bouillon (1) , Xavier Pannecoucke (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

For the first time, di-, tri-and tetrasubstituted pentafluorosulfanylated pyrrolidines have been efficiently synthetized via 1,3-dipolar cyclo-addition. In the case of tetra-substituted pyrrolidines, an unusual mixture of 1/1 regioisomers was obtained. Theoretical calculations have been carried out and the regioselectivity has been explained compared to the results previously obtained in the trifluoromethylated pyrrolidine series.

Domaines: Chimie organique; Chimie analytique; Catalyse; Chemo-informatique; Chimie thérapeutique; Chimie théorique et/ou physique

Ewelina Falkowska, Vincent Tognetti, Laurent Joubert, Philippe Jubault, J.-P. Bouillon, et al.. First efficient synthesis of SF 5 -substituted pyrrolidines using 1,3-dipolar cycloaddition of azomethine ylides with pentafluorosulfanyl-substituted acrylic esters and amides. RSC Advances, 2015, 5 (9), pp.6864-6868. ⟨10.1039/c4ra14075c⟩. ⟨hal-01149543⟩