Enantioselective bioreduction of (E)-1-phenyl-1,2-alkanedione 2-(O-methyloxime) |
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| Institution: | 1. Department of Medicinal Chemistry and Key Laboratory of Drug-Targeting of Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China;2. College of Chemistry and Environment Protection Engineering, Southwest University for Nationalities, Chengdu 610041, China;3. College of Chemistry and Chemical Engineer, Lanzhou University, Lanzhou 730000, China;4. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;5. Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, China;1. Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710127, PR China;2. Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, PR China;1. Department of Chemistry, FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada;2. L''Oréal R&I, 1 avenue Eugène Schueller, Aulnay-sous-Bois, France;3. L''Oréal R&I, 133 Terminal Av, Clark, NJ 07066, USA;1. Wageningen University, Laboratory of Food Chemistry, P.O. Box 17, 6700 AA Wageningen, The Netherlands;2. FeyeCon Carbon Dioxide Technologies, Rijnkade 17a, 1382 GA Weesp, The Netherlands |
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| Abstract: | The baker's yeast reduction of (E)-1-phenyl-1,2-alkanedione 2-(O-methyloxime), PhC(O)C(NOMe)R (R=Me, Et, n-Pr, n-Bu), gave the corresponding optically active alcohols PhCH2OHC(NOMe)R in 88–99% enantiomeric excess and 48–75% chemical yield. The R configuration was proposed for these alcohols based on circular dichroism analysis. Only the phenylglyoxal O-methylaldoxime (R=H) gave poor enantiomeric excess (65%) and chemical yield (14%). These compounds are potential chiral building blocks for the stereoselective synthesis of norephedrine analogs. |
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