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Enantioselective epoxidations of alkenes catalyzed by (salen)Mn(III) in aqueous surfactant systems
Authors:Francesco P Ballistreri  Lucia Brinchi  Raimondo Germani  Gianfranco Savelli  Gaetano A Tomaselli  Rosa M Toscano
Institution:aDipartimento Scienze Chimiche, University of Catania, Viale A. Doria, 6-95125 Catania, Italy;bCEMIN, Centro di Eccellenza Materiali Innovativi Nanostrutturati, Dipartimento di Chimica, University of Perugia, Via Elce di Sotto, 8-06123 Perugia, Italy
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-β-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-β-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.
Keywords:Enantioselectivity  Epoxidation  Alkenes  Salen  Surfactant  Amine oxide
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