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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Activation of oxaziridines by lewis acids: application in enantioselective sulfoxidation
Sébastien Schoumacker1, Olivier Hamelin, Sébastien Téti
1Laboratoire 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.
Abstract:
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.
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