CATALYTIC ENANTIOSELECTIVE ALLYLIC OXIDATION OF OLEFINS WITH COPPER(I) CATALYSTS AND NEW PERESTER OXIDANTS

Abstract Asymmetric allylic oxidation of cyclic olefins using a catalytic amount of copper(I) bisoxazoline complexes and new peresters was investigated to give allylic benzoate esters in high selectivity (∼80%ee), yield (70–80%), and at reasonable rates (5–7 d) at −20 °C in acetonitrile. Cyclohexene reacted with para -chloro tert -butylperbenzoate and 15 mol% diphenylbisoxazoline-copper(I) hexafluorophosphate to give benzoate product in 83% yield and 75% ee.