Chiral nonracemic C2-symmetry biphenyls by desymmetrization of 6, 6', 2, 2'-tetramethoxy-1, 1'-biphenyl (Articolo in rivista)

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  • Chiral nonracemic C2-symmetry biphenyls by desymmetrization of 6, 6', 2, 2'-tetramethoxy-1, 1'-biphenyl (Articolo in rivista) (literal)
Anno
  • 2000-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/S0957-4166(00)00410-9 (literal)
Alternative label
  • Delogu, G.; Fabbri, D.; Dettori, M. A.; Forni, A.; Casalone, G. (2000)
    Chiral nonracemic C2-symmetry biphenyls by desymmetrization of 6, 6', 2, 2'-tetramethoxy-1, 1'-biphenyl
    in Tetrahedron: asymmetry (Print); Elsevier Science Ltd., Oxford (Regno Unito)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Delogu, G.; Fabbri, D.; Dettori, M. A.; Forni, A.; Casalone, G. (literal)
Pagina inizio
  • 4417 (literal)
Pagina fine
  • 4427 (literal)
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  • Impact Factor 2000: 2.797; SJR 2000: Inorganic Chemistry, Q1 (literal)
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  • http://www.sciencedirect.com.pros.lib.unimi.it/science/article/pii/S0957416600004109 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 11 (literal)
Rivista
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  • 11 (literal)
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  • 21 (literal)
Note
  • Scopu (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Istituto CNR Applicazione delle Tecniche Chimiche Avanzate ai Problemi Agrobiologici, Via Vienna 2, I-07100 Sassari, Italy; Centro del CNR per lo Studio delle Relazioni tra Struttura e Reattivita` Chimica, Via Golgi 19, I-20133 Milan, Italy (literal)
Titolo
  • Chiral nonracemic C2-symmetry biphenyls by desymmetrization of 6, 6', 2, 2'-tetramethoxy-1, 1'-biphenyl (literal)
Abstract
  • Regioselective bromination of the title biphenyl 1 at the 3 and 3' positions and simultaneous desymmetrization of the biphenyl has been achieved. Metal-halide exchange at the 3,3' positions facilitated the introduction of functional groups in good yield. Regioselective reduction was obtained by using (CH3)(3)SiI, L-Selectride and HI according to the functional groups on the biphenyls. Resolution of 6,6',2,2'-tetramethoxy-3,3'-dimethyl-1,1'-biphenyl 3 was achieved by its conversion to the corresponding phosphorothioamidate diastereomers of the (S)-(-)-alpha -methylbenzylamine. The absolute configuration of (M)-(+)-3 was confirmed by X-ray analysis of the corresponding diastereomer. (literal)
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