Enantioselective epoxidations of alkenes catalyzed by (salen)Mn(III) in aqueous surfactant systems

An aqueous reaction medium, based on a surfactant solution of diethyltetradecylamine N-oxide (AOE-14), was developed for the enantioselective epoxidation of 1,2-dihydronaphthalene and of various cis-beta o-alkyl styrenes with increasing hydrophobicity, using bleach as oxidant and the Jacobsen chiral (salen)Mn(III) as catalyst. AOE-14 is able to both solubilize all reactants in water and bind the metal of the salen complex acting as coligand. Its use leads to good yields (> 75%) and to ee values ranging from 75% up to 91% even in the case of cis-beta-alkyl styrenes where lower cis/trans epoxide ratios are observed. The ratio of surfactant/substrate used is 1:1 or 4:1, much lower than those generally used in the literature. (c) 2008 Elsevier Ltd. All rights reserved.