Enzyme-catalysed improved resolution of (RS)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropyl-1-butanol |
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| Affiliation: | 1. Department of Chemistry, Yonsei University, Shinchon, Seoul 120-749, South Korea;2. Life Sciences Division, Korea Institute of Science and Technology, PO Box 131, Cheongryang, Seoul 130-650, South Korea;1. Chemours Company, Fluoroproducts, Experimental Station, PO Box 80262, Wilmington, DE 19880-0262, USA;2. DuPont Central Research and Development, Experimental Station, PO Box 80328, Wilmington, DE 19880-0328, USA;1. Department of Forest Industrial Engineering, Faculty of Forestry, Kastamonu University, Kastamonu, 37100, Turkey;2. Department of Chemistry, Faculty of Art and Science, Kastamonu University, Kastamonu, 37100, Turkey;3. Biomedical Engineering Department, Faculty of Engineering and Architecture, Kastamonu University, Kastamonu, Turkey;4. Department of Medical Services and Techniques, Vocational High School of Health Services, Giresun University, Giresun, Turkey;5. Department of Infectious Diseases, Faculty of Medicine, Adıyaman University, Adıyaman, Turkey;1. School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China;2. School of Technology and Physical Science, ShanghaiTech University, Shanghai 201210, China;1. School of Civil Engineering and Architecture, Anhui University of Science and Technology (AUST), Huainan, 232001, Anhui, China;2. State Key Laboratory of Mining-induced Response and Disaster Prevention and Control in Deep Coal Mines, AUST, Huainan, 232001, Anhui, China;3. School of Chemical Engineering, AUST, Huainan, 232001, Anhui, China;4. Graduate School of Engineering Science and Technology, National Yunlin University of Science and Technology, Yunlin, 64002, Taiwan, ROC |
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| Abstract: | Resolutions of (RS)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropyl-1-butanol 1 using various enzymes were performed. Among them, Pseudomonas fluorescens resolved it with moderate stereoselectivity (E=13) and reacted faster with the (S)-enantiomer. To optimize enzyme-catalysed reaction conditions for the resolution, the effect of solvents and additives was studied. In n-hexane:ethyl acetate (9:1), both reaction rate and selectivity were high. When pyridine, potassium carbonate and molecular sieves were used as additives, the enantiomeric excess of the (R)-enantiomer was 99, 99 and 98% at 52–60% conversion, respectively. However, in diisopropyl ether, the enantiomeric excess of unreacted alcohol (R)-1 was up to 99% at 70% conversion without additives. |
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