Stereoselective oxazaborolidine-borane reduction of biphenyl methyl diketones: influence of biphenyl substitution pattern (Articolo in rivista)

Type
Label
  • Stereoselective oxazaborolidine-borane reduction of biphenyl methyl diketones: influence of biphenyl substitution pattern (Articolo in rivista) (literal)
Anno
  • 2004-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tet.2004.08.066 (literal)
Alternative label
  • Delogu G.; Dettori M. A.; Patti A.; Pedotti S. (2004)
    Stereoselective oxazaborolidine-borane reduction of biphenyl methyl diketones: influence of biphenyl substitution pattern
    in Tetrahedron (Oxf., Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Delogu G.; Dettori M. A.; Patti A.; Pedotti S. (literal)
Pagina inizio
  • 10305 (literal)
Pagina fine
  • 10310 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://www.sciencedirect.com/science/article/pii/S0040402004014097 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 60 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 6 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 45 (literal)
Note
  • ISI Web of Science (WOS) (literal)
  • Scopu (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Istituto di Chimica Biomolecolare del CNR-Sez. di Sassari, Traversa la Crucca, regione Baldinca, Li Punti, 07040 Sassari, Italy Istituto di Chimica Biomolecolare del CNR-Sez. di Catania, Via del Santuario 110, I-95028 Valverde CT, Italy (literal)
Titolo
  • Stereoselective oxazaborolidine-borane reduction of biphenyl methyl diketones: influence of biphenyl substitution pattern (literal)
Abstract
  • The stereoselective oxazaborolidine-borane reduction of biphenyl methyl diketones with different substitution patterns on the biaryl unit was investigated, with the aim to better rationalize the factors influencing the diastereo- and enantioselectivity of the reaction for this class of compounds. The observed stereoselectivity in the reduction of diketones 6 and 7, possessing a methoxy group in the meta position with respect to the carbonyl group, is clearly dependent on the experimental conditions. The presence of an asymmetric centre in the intermediate hydroxyketone influences the global stereoselectivity in the reduction of 5 and 6, as indicated from the different selectivity ratios determined for each step of reaction. (literal)
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