text: 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.
  The high reactivity of trifluoroperacetic acid relative to other peroxy acids allows it to successfully oxidize relatively electron-poor alkenes such as 1-hexene and α,β-unsaturated esters such as methyl methacrylate, substrates that are generally resistant to peroxy-acid epoxidation.  Including additional buffered trifluoroacetic acid in the mixture gives a vicinal hydroxy–trifluoroacetate structure instead of an epoxide, which can be converted to the diol by treatment with acidic methanol, such as in the following conversion of 1-dodecene to 1,2-dodecanediol.
  In the case of an allyl alcohol compound with a proximate carbonyl functional group, the epoxide can undergo a ring-expansion reaction to form a dioxolane.  The process below was used as part of the total synthesis of neosporol, a natural product:
  The preparation of the isomeric compound sporol involved a similar dioxolane formation. In this case, the use of trifluoroperacetic acid derived from hydrogen peroxide, which therefore presumably contained traces of water, gave mostly a hemiacetal rather than the closed-ring dioxolane. The use of the urea complex, which gave a water-free material, successfully gave the dioxolane as the major product.  The dioxolane is expanded to the 1,3-dioxane system found in sporol at a later step in the synthesis.