Efficient dynamic kinetic resolution of secondary alcohols with a novel tetrafluorosuccinato ruthenium complex |
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| Institution: | 1. Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, PO Box 513, 5600 MB Eindhoven, The Netherlands;2. Process Development Group, Eindhoven University of Technology, PO Box 513, 5600 MB Eindhoven, The Netherlands;1. School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, PR China;2. Department of Chemistry, College of Saint Benedict and Saint John’s University, MN 56374, USA;1. Department of Organic Chemistry, Institute of Chemical Sciences, Faculty of Science, P.J. ?afárik University, Moyzesova 11, 040 01 Ko?ice, Slovak Republic;2. Department of Pharmacology, Faculty of Medicine, P.J. ?afárik University, SNP 1, 040 66 Ko?ice, Slovak Republic;3. Division of Biological Sciences, Graduate School of Science, Frontier Research Center for Post-Genomic Science and Technology, Hokkaido University, Kita-ku, Sapporo 001-0021, Japan;4. Department of Analytical Chemistry, Institute of Chemical Sciences, Faculty of Science, P.J. ?afárik University, Moyzesova 11, 040 01 Ko?ice, Slovak Republic;1. Department of Chemistry, Hue University’s College of Sciences, 77 Nguyen Hue, Hue, Viet Nam;2. The University of Danang – Campus in Kon Tum, 704 Phan Dinh Phung, Kon Tum, Viet Nam;3. Institute of Research and Development, Duy Tan University, 03 Quang Trung, Danang, Viet Nam;4. Department of Chemistry, The University of Danang – University of Science and Technology, 54 Nguyen Luong Bang, Lien Chieu, Danang, Viet Nam;1. Institut de Chimie Moléculaire de Reims, UMR CNRS 7312, Université de Reims, 51687 Reims Cedex, France;2. Institut de Chimie Organique et Analytique, UMR CNRS 7311, Université d’Orléans, 45067 Orleans Cedex, France;3. Unité de Recherche Vignes et Vins de Champagne, EA 4707, Université de Reims, 51687 Reims Cedex, France;4. Centre de Biophysique Moléculaire Numérique, Université de Liège, Passage des Déportés, 2, 5030 Gembloux, Belgium |
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| Abstract: | Dynamic kinetic resolution (DKR) of a series of secondary alcohols has been conducted with a novel dinuclear ruthenium complex, bearing tetrafluorosuccinate and (rac)-BINAP ligands as the racemization catalyst. Novozym 435 has been used as the enzyme, and isopropyl butyrate as the acyl donor. Five substrates underwent DKR successfully: an aliphatic and an aromatic secondary alcohol, an aromatic alcohol with an electron-withdrawing substituent on the phenyl ring, an aromatic alcohol bearing an electron-donating substituent on the ring and a heteroaromatic secondary alcohol. The catalyst performed optimally at 70 °C. Typically the reaction reached complete conversion within 1 day with 0.1 mol % of racemization catalyst relative to the substrate. The addition of the ketone corresponding to the substrate stabilizes the active Ru complex and, therefore, increases the rate of the reaction. |
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