4.7 Article

Oxaziridine-mediated amination of branched allylic sulfides: Stereospecific formation of allylic amine derivatives via [2,3]-sigmatropic rearrangement

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 10, Pages 4028-4030

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo060369s

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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.

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