Synthesis of novel planar-chiral [2.2]paracyclophane derivatives as potential ligands for asymmetric catalysis |
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Authors: | Michael Kreis Stefan Bräse |
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Institution: | a Institut für Organische Chemie, Universität Karlsruhe (TH), Fritz-Haber-Weg 6, D-76131 Karlsruhe, Germany b Institut für Anorganische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, D-53121 Bonn, Germany |
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Abstract: | The synthesis of a variety of new 4,5-disubstituted 2.2]paracyclophane derivatives has been achieved employing different cross-coupling reactions. By this methodology, a heteroatom-variation of successful catalyst ligands was achieved, giving rise to a modular ligand system. The X-ray structure of 4-hydroxy-5-(1′-hydroxy-1′-phenylethyl)-2.2]paracyclophane was determined to elucidate the configuration. Additionally, a diastereoselective synthesis of planar- and central-chiral 4-(2.2]paracyclophanyl)ethylamine was achieved, thus resulting in a planar- and central-chiral phenyl ethylamine analogue. |
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Keywords: | [2 2]paracyclophane Asymmetric catalysis Cross-coupling reaction Planar chirality |
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