Hydrogen-Bond-Mediated Enantio- and Regioselectivity in a Ru-Catalyzed Epoxidation Reaction

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     «

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...     »

ISI Document Delivery No.: 680AK Times Cited: 20 Cited Reference Count: 51 Fackler, Philipp Berthold, Carola Voss, Felix Bach, Thorsten Deutsche Forschungsgemeinschaft [Ba 1372-10]; Universitat Bayern e.V.; TUM Graduate School This project was supported by the Deutsche Forschungsgemeinschaft (Ba 1372-10), the Universitat Bayern e.V. (Predoctoral Scholarship to C.B.), and the TUM Graduate School. We thank Wacker-Chemie (Munich) and Umicore (Hanau) for the donation of chemicals and Dr. S. Huber (TU Munchen) for conducting the semiempirical calculations. 20 Amer chemical soc Washington     «

ISI Document Delivery No.: 680AK Times Cited: 20 Cited Reference Count: 51 Fackler, Philipp Berthold, Carola Voss, Felix Bach, Thorsten Deutsche Forschungsgemeinschaft [Ba 1372-10]; Universitat Bayern e.V.; TUM Graduate School This project was supported by the Deutsche Forschungsgemeinschaft (Ba 1372-10), the Universitat Bayern e.V. (Predoctoral Scholarship to C.B.), and the TUM Graduate School. We thank Wacker-Chemie (Munich) and Umicore (Hanau) for the donation of chemicals and Dr. S. Huber...     »