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A study, via isotopic labeling, of the stereoselective processes in a Shi-type epoxidation, has revealed that the chiral platform provided by the catalyst mediates the transfer of the pro-S “O” of the related dioxirane species to the alkene in a doubly stereoselective manner.

Graphical abstract: Dioxirane mediated asymmetric epoxidations: stereochemical studies via isotopic labeling

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