Diastereoselective epoxidation and bishydroxylation of cyclic tert-butyl allyl peroxides

Add time:07/14/2019    Source:sciencedirect.com

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 tBuOO 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 18–23a,b. Analogous high anti-selectivity was observed in the OsO4-catalyzed bishydroxylation of 1 – 6 with tBuOOH to the corresponding diols 18c, 20c, 25, 26a,b, 22c, and 27a,b.

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