Acid promoted enantioselective oxygen-atom transfer from N-alkyl binaphthyl-derived oxaziridines onto sulfides

Akhatou, Abdeslam;Rahimi, Maryam;Cheboub, Karima;Ghosez, Léon;Hanquet, Gilles
(2007) Tetrahedron — Vol. 63, n° 27, p. 6232-6240 (2007)

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Authors
  • Akhatou, Abdeslam
    Author
  • Rahimi, Maryam
    Author
  • Cheboub, KarimaUCLouvain
    Author
  • Ghosez, LéonUCLouvain
    Author
  • Hanquet, Gilles
    Author
Abstract
Acid-promoted asymmetric sulfoxidations of prochiral sulfides using binaphthyl-derived oxaziridines have been studied. The reactions of dialkyl or aryl-alkyl sulfides gave good yields of the corresponding sulfoxides with enantiopurities ranging from 20% to 80%. The influence of temperature and strength of the acid catalyst on enantioselectivity was studied. The absolute configuration of the resulting major enantiomer varied with the structure of the sulfide. (c) 2007 Elsevier Ltd. All rights reserved.
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Citations

Akhatou, A., Rahimi, M., Cheboub, K., Ghosez, L., & Hanquet, G. (2007). Acid promoted enantioselective oxygen-atom transfer from N-alkyl binaphthyl-derived oxaziridines onto sulfides. Tetrahedron, 63(27), 6232-6240. https://doi.org/10.1016/j.tet.2007.02.119 (Original work published 2007)