Journal
TETRAHEDRON
Volume 71, Issue 42, Pages 8067-8076Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.08.050
Keywords
Fluorine; Pentafluorosulfanyl; 1,3-Dipolar cycloaddition; Heterocycle; Isoxazolidine
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Funding
- MESR (Ministere de l'Enseignement Superieur et de la Recherche)
- Region Haute-Normandie (CRUNCh program)
- CNRS
- Rouen University
- INSA of Rouen
- Labex SynOrg [ANR-11-LABX-0029]
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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. (C) 2015 Elsevier Ltd. All rights reserved.
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