Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation: complementary approaches |
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| Affiliation: | 1. Division of Industrial Microbiology, Department of Agrotechnology and Food Sciences, Wageningen University and Research Centre, PO Box 8129, 6700 EV Wageningen, The Netherlands;2. Department of Chemical and Environmental Engineering, University of Arizona, PO Box 210011, Tucson, AZ 85721-0011, USA;3. Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands;4. Laboratory of Organic Chemistry, Wageningen University and Research Centre, Dreijenplein 8, 6703 HB Wageningen, The Netherlands;5. DSM Research, Life Science Products, PO Box 18, 6160 MD Geleen, The Netherlands;6. DSM Research, postpoint 624-305, PO Box 1, 2600 MA Delft, The Netherlands;1. School of Chemistry, College of Science, University of Tehran, P.O. Box 14155-6455, Tehran, Islamic Republic of Iran;2. Department of Materials Science and Technology, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla, Thailand;3. Department of Chemistry, Biology and Biotechnologies, University of Perugia, Perugia, Italy;1. Institute of Bioengineering, Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, PR China;2. College of Life Science, Department of Chemistry Material, Huzhou University, Huzhou 313000, PR China;1. AVT—Biochemical Engineering, RWTH Aachen University, Worringerweg 1, D-52074 Aachen, Germany;2. AVT—Enzyme Process Technology, RWTH Aachen University, Worringerweg 1, D-52074 Aachen, Germany;3. Department of Biotechnology, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan |
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| Abstract: | Prochiral aryl and dialkyl ketones were enantioselectively reduced to the corresponding alcohols using whole cells of the white-rot fungus Merulius tremellosus ono991 as a biocatalytic reduction system and ruthenium(II)–amino alcohol and iridium(I)–amino sulfide complexes as metal catalysts in asymmetric transfer hydrogenation. Comparison of the results showed that the corresponding chiral alcohols could be obtained with moderate to high enantioselectivities (e.e.s of up to 98%). The biocatalytic and transfer hydrogenation approaches appear to be complementary. The biocatalytic approach is the most suitable for the enantioselective reduction of chloro-substituted (aryl) ketones, whereas in the reduction of α,β-unsaturated compounds excellent results were obtained using the catalytic hydrogenation protocol. |
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