Enantioselective epoxidation of isoflavones by Jacobsen's Mn(III)salen catalysts and dimethyldioxirane oxygen-atom source |
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| Institution: | 1. Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany;2. Department of Organic Chemistry, Lajos Kussuth University, Egyetem tér 1, H-4010 Debrecen, Hungary;3. Max-Planck-Institut für Festkörperforschung, Heisenbergstrasse 1, D-70506 Stuttgart, Germany;4. Technical Analytical Research Group of the Hungarian Academy of Sciences, Institute for General and Analytical Chemistry of the Technical University, St. Gellért tér 4, H-1111 Budapest, Hungary;1. Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Ireland;2. Department of Chemistry and School of Pharmacy, Synthesis and Solid State Pharmaceutical Centre, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland;1. Department of Pharmacology, School of Basic Medical Sciences, Shandong University, Jinan, 250012, China;2. Department of Clinical Pharmacy, Qilu Hospital of Shandong University, Jinan, 250012, China;3. School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, China;4. Department of Neurosurgery, Provincial Hospital, Shandong University, Jinan, 250021, China;1. State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Nanjing University, Nanjing 210046, China;2. State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200000, China |
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| Abstract: | The catalytic enantioselective epoxidation of the isoflavones 1a–f has been performed by the Mn(III)salen complexes (R,R)-3 and (S,S)-3 as catalysts and dimethyldioxirane as the oxygen-atom source to afford optically active isoflavone epoxides 2a–f. The absolute configuration of the nonracemic epoxides 2 have been determined by X-ray diffraction analysis. Our present results constitute the first examples of the preparation of optically active isoflavone epoxides. |
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