Hydrogen-bond-mediated enantio- and regioselectivity in a Ru-catalyzed epoxidation reaction |
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Authors: | Fackler Philipp Berthold Carola Voss Felix Bach Thorsten |
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Affiliation: | Lehrstuhl fu?r Organische Chemie I and Catalysis Research Center (CRC), Technische Universita?t Mu?nchen, Lichtenbergstr. 4, 85747 Garching, Germany. |
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Abstract: | A chiral epoxidation catalyst based on a tricyclic octahydro-1H-4,7-methanoisoindol-1-one scaffold, in which a hydrogen bonding site and the catalytically active ruthenium center are spatially separated, was synthesized. It was shown that epoxidation reactions in such a supramolecular catalyst occur with high enantio- and regioselectivity because the hydrogen bonds expose the substrate to the ruthenium porphyrin complex with a clear conformational preference. The epoxidation of 3-vinylquinolone proceeded in up to 95% ee (71% yield). |
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