Reaction of branched allylic sulfides with the N-Boc-oxaziridine 1 results in [2,3]-sigmatropic rearrangement of the intermediate allylic N-Boc-sulfimides with a high level of chirality transfer. The first example of formation of a quaternary stereocenter using this transformation is reported.

A novel N-Boc-oxaziridine is reported, derived from diethyl ketomalonate, which effects efficient amination of sulfides to sulfimides. The reagent is applied to the [2,3]-sigmatropic rearrangement of allylic sulfimides.

Amination of propargylic sulfides with a ketomalonate-derived oxaziridine under metal free conditions gives N-Boc-N-allenylsulfenimides via [2,3]-sigmatropic rearrangement.

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