Regioselective Oxyfunctionalization of Bridgehead Adamantane Derivatives

The reactions of bridgehead adamantane derivatives with perfluoro-cis-2-n-butyl-3-n-propyloxaziridine have been studied. The oxyfunctionalization process was found to proceed with excellent regioselectivity affording 3-substituted adamantan-1-ols in preparative chemical yields. The regioselectivity of the reaction was shown to tolerate various organic functional groups such as halogen, haloalkyl, hydroxyl, carboxyl and carboalkoxyl. Mild reaction conditions, simplicity of the experimental procedure, high selectivity and chemical yields render this process an immediately useful and generalized approach to synthetically challenging polyfunctional adamantane derivatives