Allyl-substituted alkenes, diastereoselective epoxidations

Oxone has also been used in the metalloporphyrin-catalyzed diastereoselective epoxidation of allyl-substituted alkenes (eq 109) and in the manganese, salen-polystyrene-bound imidazole catalyzed deoxidation of alkenes (eq 110). ... 

Before commencing, the attention of the reader is drawn to our usage of the terms enantiofacial selectivity and diastereoselectivity. The usage in this chapter does not conform to the strictest possible definitions of these terms. In particular, enantiofacial selectivity is used with reference to the selection and delivery of oxygen by the epoxidation catalyst to one face of the alkene in preference to the other. This usage extends to chird allylic alcohols (primarily the 1-substituted allylic alcohols) when the focus of the discussion is on face selection in the epoxidation process. Diastereoselectivity is used in the discussion of kinetic resolution, when the generation of diastereomeric compounds is emphasized. 

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