The Prilezhaev reaction involves the conversion of an alkene to an epoxide using a peracid as the oxidant and was first reported in 1909. The reaction has been used as the final step of the synthesis of scopine, a tropane alkaloid. In this approach, a [4+3] cycloaddition mediated by diiron nonacarbonyl is used to construct the bicyclic skeleton, the hydroxyl functional group is then introduced by diastereoselective reduction of the ketone with diisobutylaluminum hydride, and the preparation completed with a Prilezhaev trifluoroperacetic acid epoxidation.
