Synthesis of SF5-substituted isoxazolidines using 1, 3-dipolar cycloaddition reactions of nitrones with pentafluorosulfanyl acrylic esters and amides. Issue 42 (21st October 2015)

• Record Type: Journal Article
• Authors: Falkowska, Ewelina; Laurent, Mathieu Y.; Tognetti, Vincent; Joubert, Laurent; Jubault, Philippe; Bouillon, Jean-Philippe; Pannecoucke, Xavier
• Is Part Of: Tetrahedron. Volume 71:Issue 42(2015)
• Page Start: 8067
• Page End: 8076
• Publication Date: 2015-10-21
• Subjects: Fluorine -- Pentafluorosulfanyl -- 1, 3-Dipolar cycloaddition -- Heterocycle -- Isoxazolidine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.08.050
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 1, 3-Dipolar cycloadditions of nitrones with pentafluorosulfanyl-substituted acrylic ester and amides afforded new trisubstituted pentafluorosulfanylated isoxazolidines in moderate yields as 4-SF5 -regioisomers. Theoretical calculations were carried out and the regioselectivity could be explained by the fact that the 5-SF5 -regioisomer probably undertook a spontaneous degradation in the reaction medium via the loss of pentafluorosulfanyl anion. Diastereoselectivity of the 1, 3-dipolar cycloadditions was also assessed according to NMR and X-ray diffraction analysis. Graphical abstract: