Enhanced enantioselectivity in the heterogeneous catalytic hydrogenation of acetoacetate esters into the corresponding 3-hydroxybutyrates using commercial nickel powder |
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| Institution: | 1. Graduate School of Science and Engineering for Research, University of Toyama, Gofuku, Toyama 930-8555, Japan;2. Metek Co., Ltd, 1 Warada-cho, Kamitoba, Minami-ku, Kyoto 601-8133, Japan;3. Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan;1. Physics Department & Shanghai Key Laboratory of Magnetic Resonance, East China Normal University, Shanghai 200062, China;2. UCCS, University Lille North of France, Villeneuve d’Ascq 59652, France;1. Institute of Biophysical Chemistry & Center for Biomolecular Magnetic Resonance, Goethe University, Max-von-Laue-Str. 9, D-60438 Frankfurt, Germany;2. Institute of Biochemistry, Goethe University, Max-von-Laue-Str. 9, D-60438 Frankfurt, Germany;3. Vertex Pharmaceuticals Inc., Cambridge, MA 02139, USA;1. School of Pharmacy, Shanghai University of Traditional Chinese Medicine, 1200 Cailun Road, Shanghai, 201203, People''s Republic of China;2. Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai, 201203, People''s Republic of China;1. School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, PR China;2. Key Laboratory of Henan Province for Drug Quality and Evaluation, Zhengzhou 450001, PR China;3. Key Laboratory of Technology of Drug Preparation, Ministry of Education, Zhengzhou 450001, PR China;4. Collaborative Innovation Center of New Drug Research and Safety Evaluation, Zhengzhou 450001, Henan Province, PR China |
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| Abstract: | Heterogeneous catalytic hydrogenation of acetoacetic acid esters over tartaric acid/NaBr-modified Ni powder was determined to be a critical function of the steric bulk of the ester moiety to afford quantitatively 3-hydroxybutyrate in 94% enantiomeric excess when ethyl and i-butyl esters are used, providing a facile route to optically active 3-hydroxybutyrates. |
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