Microbial and homogenous asymmetric catalysis in the reduction of 1-[3,5-bis(trifluoromethyl)phenyl]ethanone |
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Affiliation: | 1. Key Laboratory of Industrial Biotechnology of the Ministry of Education & School of Biotechnology, Jiangnan University, Wuxi 214122, PR China;2. National Key Laboratory for Food Science, Jiangnan University, Wuxi 214122, PR China;3. Center for Advanced Biotechnology and Medicine, Rutgers University, Piscataway, NJ 08854, USA |
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Abstract: | Two complementary approaches for the enantioselective reduction of 1-[3,5-bis(trifluoromethyl)phenyl]ethanone 1 are described and compared: microbial versus asymmetric reduction of ketones through asymmetric hydrogen transfer. Among the various microorganisms screened, Lactobacillus kefir and Aspergillus niger reduced ketone 1 to the corresponding (R)-alcohol (R)-2. The (S)-alcohol (S)-2 was obtained by reduction of 1 using homogenous asymmetric catalysis. The configuration of the alcohol in both the biocatalysis and hydrogen transfer approaches was controlled by the choice of the enzyme and by the configuration of ligands, respectively. Both enantiomers were obtained in high yield and ee. |
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