Activation of oxaziridines by lewis acids: application in enantioselective sulfoxidation.
The preparation of new and easily accessible chiral N-alkyloxaziridines for asymmetric sulfides oxidation was investigated. Most significantly, we report here that inert N-alkyloxaziridines can be activated by Lewis acids to achieve a fast, selective, and efficient oxygen atom transfer to sulfides. Asymmetric sulfoxidation by three new chiral oxaziridines (two of them were structurally characterized by X-ray analysis) afforded enantioselectivities ranging from 22% to 63% ee with the simplest aryl alkyl sulfides.
Schoumacker
Sébastien
S
Laboratoire de Chimie et Biochimie des Centres Rédox Biologiques, DRDC-CB, UMR 5047 Université Joseph Fourier/CEA/CNRS, CEA Grenoble, 17 avenue des Martyrs, 38054 Grenoble Cedex, France.
Hamelin
Olivier
O
Téti
Sébastien
S
Pécaut
Jacques
J
Fontecave
Marc
M