Diastereoselective epoxidation and bishydroxylation of cyclic tert-butyl allyl peroxides

Article abstract of DOI:10.1016/0040-4020(96)00787-9

The epoxidation and the OsO₄-catalyzed bishydroxylation of cyclic tert-butyl allyl peroxides 1 - 6 have been investigated. The epoxidation of 1, 2, 3, 5 carried out with four different oxidants proceeded mainly with high anti-selectivity referred to the ¹BuOO group leading to the epoxides 12-15a,b. The nucleophilic ring-opening of the epoxides 12-15a,b was accomplished with H₂O or MeOH catalyzed by BF₃*Et₂O and proceeded with very high regio- and diastereoselectivity yielding new functionalized tert-butyl peroxides 18-23 a,b. Analogous high antiselectivity was observed in the OsO₄-catalyzed bishydroxylation of 1-6 with ¹BuOOh to the corresponding diols 18c, 20c, 25, 26a,b, 22c, and 27a,b.