A Combined Theoretical and Experimental Investigation on the Enantioselective Oxidation of Aryl Benzyl Sulfides in the Presence of a Chiral Titanium Catalyst (Articolo in rivista)

Type
Label
  • A Combined Theoretical and Experimental Investigation on the Enantioselective Oxidation of Aryl Benzyl Sulfides in the Presence of a Chiral Titanium Catalyst (Articolo in rivista) (literal)
Anno
  • 2009-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/chem.200902110 (literal)
Alternative label
  • Naso F., Capozzi M.A.M., Bottoni A., Calvaresi M., Bertolasi V., Capitelli F., Cardellicchio C. (2009)
    A Combined Theoretical and Experimental Investigation on the Enantioselective Oxidation of Aryl Benzyl Sulfides in the Presence of a Chiral Titanium Catalyst
    in Chemistry (Weinh., Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Naso F., Capozzi M.A.M., Bottoni A., Calvaresi M., Bertolasi V., Capitelli F., Cardellicchio C. (literal)
Pagina inizio
  • 13417 (literal)
Pagina fine
  • 13426 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 15 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • -Dip. di Chimica and CNR ICCOM, Bari -Dip. di Scienze Agroalimentari, Chimica e Difesa Vegetale, Univ. di Foggia -Dip. di Chimica G. Ciamician, Univ. di Bologna -Dip. di Chimica and Centro si Strutturistica Diffrattometrica, Univ. di Ferrara -CNR-Istituto di Cristallografia, Sede di Bari (literal)
Titolo
  • A Combined Theoretical and Experimental Investigation on the Enantioselective Oxidation of Aryl Benzyl Sulfides in the Presence of a Chiral Titanium Catalyst (literal)
Abstract
  • An experimental investigation of the enantioselective oxidation of aryl benzyl sulfides by tort-butyl hydroperoxide in the presence of a titanium/hydrobenzoin catalyst has shown that these sulfides are ideal substrates for this catalytic system, with negligible interference by the substituents on the aryl groups. A reaction mechanism based on DFT computations has been proposed. The DFT MPWB1K functional was used in the theoretical investigation to account for weak hydrogen-bonding and pi interactions. The computed reaction profile explains the experimentally observed enantioselectivity, which is determined by the thermodynamics of the first phase of the reaction. A detailed discussion of the hydrogen-bonding and pi interactions that drive the reaction along the observed stereochemical path is given. (literal)
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