Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 125, Issue 4, Pages 517-525Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2003.11.024
Keywords
asymmetric catalysis; coupling; fluorine; ligand; nucleophilic aromatic substitution; BINOL; F8BINOL; F4BINOL; chiral; sulfoxidation
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New partially fluorinated binaphthols were obtained using a copper-catalyzed oxidative coupling. The corresponding enantiomerically pure compounds were prepared by fractional crystallization of the corresponding bis(menthyl)carbamates. Nucleophilic aromatic substitution using oxygen- and carbon-based nucleophiles resulted in functionalized derivatives without concomitant racemization. The titanium(IV) complexes of these ligands are catalytically active in the asymmetric oxidation of sulfides. (C) 2004 Elsevier B.V. All rights reserved.
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