Chemoenzymatic synthesis of enantiomerically enriched 2-oxobicyclo[m.1.0]alkan-3-yl acetate derivatives |
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| Institution: | 1. Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey;2. Department of Chemistry, Abant ?zzet Baysal University, 14280 Bolu, Turkey;3. Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey;1. Department of Pharmacology and Glycobiology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China;2. Division of Anti-tumor Pharmacology, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences, Shanghai 201203, China;3. CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences, Shanghai 201203, China;4. Nano Science and Technology Institute, University of Science and Technology of China, Suzhou 215123, China;5. University of Chinese Academy of Sciences, Beijing 100049, China;1. Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary;2. Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary;3. Department of Biochemistry, University of Szeged, Dóm tér 9, H-6720 Szeged, Hungary;1. Department of Theoretical Mechanics, Tomsk State University, Tomsk, Russia;2. Department of Nuclear and Thermal Power Plants, Tomsk Polytechnic University, Tomsk, Russia;3. Department of Applied Mathematics, Babe?-Bolyai University, Cluj-Napoca, Romania;4. Department of Mechanical Engineering, Technology Faculty, F?rat University, Elazig, Turkey;5. Mechanical Engineering Department, Faculty of Engineering, King Abdulaziz University, Jeddah, Saudi Arabia;1. Research and Development Centre, Bharathiar University, Coimbatore, 641 046, India;2. Department of Chemistry, Kanchi Mamunivar Government Institute for Post–Graduate Studies and Research, Puducherry, 605 008, India;3. Rajiv Gandhi Arts and Science College, Thavalakuppam, Puducherry, 605 007, India;4. Department of Physics, S.A. Engineering College, Chennai, 600 077, India |
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| Abstract: | Racemic α′-acetoxy α,β-unsaturated cyclopentanone and cyclohexanone have been resolved into the corresponding enantiomerically enriched α′-hydroxylated and acetoxylated compounds with 96–97% ee via PLE hydrolysis. Stereoselectivity in the palladium(II)-catalyzed reaction between the enantiomerically enriched α′-acetoxylated compounds and diazomethane has been investigated. In the α′-acetoxylated cyclopentenone, preferential cyclopropanation occurs in the anti-form, whereas α′-acetoxylated cyclohexenone affords both syn- and anti-products (syn:anti, 61:36%). The relative configuration of the products was determined by NOE experiments. |
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