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Synlett 1996; 1996(11): 1054-1056
DOI: 10.1055/s-1996-5659
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Synthesis of Atropisomeric Heterotopic S-Donor Ligands through Asymmetrization of C2-Symmetry 2,2’-Disubstituted 1,1’-Binaphthalene Derivatives

Davide Fabbri, Sonia Pulacchini, Serafino Gladiali*
  • *Dipartimento di Chimica, Via Vienna 2, 07100-Sassari, Italia, Fax: (+)39-79-229559, E-mail: Gladiali@ssmain.uniss.it
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Publikationsdatum:
31. Dezember 2000 (online)

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Useful synthetic procedures for the conversion of C2 symmetry 1,1’-binaphthalene-2,2’-dithiol (BINAS) and 1,1’-binaphthalene-2,2’-diol (BINOL) into heterotopic S,S’- and heterodonor O,S-chelating atropisomeric ligands have been devised. Monoalkylation of the dithiol is successfully accomplished by asymmetrization of the corresponding dicarbamate through selective removal of one S-carbamoyl group, while asymmetrization of the diol can be more readily achieved by selective monoacylation.

S-Donor chiral ligands - binaphthalene derivatives - asymmetrization