Synthesis of SF5-substituted isoxazolidines using 1,3-dipolar cycloaddition reactions of nitrones with pentafluorosulfanyl acrylic esters and amides - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Tetrahedron Année : 2015

Synthesis of SF5-substituted isoxazolidines using 1,3-dipolar cycloaddition reactions of nitrones with pentafluorosulfanyl acrylic esters and amides

Résumé

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.
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hal-01226896 , version 1 (10-11-2015)

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Ewelina Falkowska, Mathieu Y. Laurent, Vincent Tognetti, Laurent Joubert, Philippe Jubault, et al.. Synthesis of SF5-substituted isoxazolidines using 1,3-dipolar cycloaddition reactions of nitrones with pentafluorosulfanyl acrylic esters and amides. Tetrahedron, 2015, 71 (42), pp.8067-8076. ⟨10.1016/j.tet.2015.08.050⟩. ⟨hal-01226896⟩
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