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-b-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 inwater 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-b-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.

Enantioselective Epoxidation of Alkenes Catalized by (Salen)Mn(III) in Aqueous Surfactant Systems

BRINCHI, Lucia;GERMANI, Raimondo;SAVELLI, Gianfranco;
2008

Abstract

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-b-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 inwater 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-b-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.
2008
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11391/162031
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