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Synthesis of a novel class of chiral N,N,N-tridentate pyridinebisimidazoline ligands and their application in Ru-catalyzed asymmetric epoxidations
Institution:1. The Arnold and Mabel Beckman Laboratory for Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA;2. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. (IfOK), Buchbinderstraße 5-6, D-18055, Rostock, Germany;1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;2. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, 163 Xianlin Road, Nanjing, Jiangsu 210023, China;1. Hangzhou Normal University, Hangzhou, P. R. China;2. Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, P. R. China;1. Department of Chemistry, Zhejiang Sci-Tech University, Xiasha Campus, Hangzhou, Zhejiang Province 310018, People’s Republic of China;2. Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany;1. Department of Chemistry, Zhejiang Sci-Tech University, Xiasha Campus, Hangzhou 310018, People’s Republic of China;2. Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
Abstract:A new class of easily tunable N,N,N-pyridinebisimidazoline (pybim) ligands have been synthesized. The synthesis and tunability of these chiral tridentate ligands are much easier and flexible compared to the popular pyboxes, making the former a suitable ligand tool box for various asymmetric transformations. Ruthenium complexes of the new ligands were synthesized and applied in the asymmetric epoxidation of olefins using hydrogen peroxide as the oxidant. Excellent yields and moderate to good enantioselectivities were achieved in the epoxidation of aromatic olefins.
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