New insights into the titanium-mediated enantioselective oxidation of fluorinated aryl benzyl sulfides and aryl phenacyl sulfides |
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Authors: | Maria Annunziata M Capozzi Vanni Frascaro Gennaro Pescitelli Cosimo Cardellicchio |
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Institution: | 1. CNR ICCOM - Dipartimento di Chimica, Università di Bari, via Orabona 4, 70125, Bari, Italy;2. Dipartimento di Chimica, Università di Bari, via Orabona 4, 70125, Bari, Italy;3. Dipartimento di Chimica e Chimica Industriale, Università di Pisa, via Moruzzi 13, 56124, Pisa, Italy |
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Abstract: | A fruitful switch from tert-butyl to cumene hydroperoxide was able to overcome a difficulty arose in the enantioselective oxidation of fluorinated aryl benzyl sulfide with hydroperoxides in the presence of a titanium/(S, S)-hydrobenzoin catalyst. New experiments show the complementarity of the old and the new protocols and indicate unequivocally the right choice leading to the corresponding highly enantioenriched sulfoxides. Moreover, in a totally unexpected way, the new protocol was able to overcome another difficulty arose in another field of research, that is the enantioselective oxidation of a fluorinated aryl phenacyl sulfide. Also in this case, the complementarity of behavior is acting. Finally, this investigation gives new support to the attribution of configuration of sulfoxides with ECD techniques, but only if the protocol outlined in our past research was followed thoroughly. |
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Keywords: | Catalysis Sulfoxide Circular dichroism Oxidation mechanism Hydrobenzoin |
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