First asymmetric aminohydroxylation of acrylamides |
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| Affiliation: | 1. Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität, Gerhard-Domagk-Straße 1, D-53121 Bonn, Germany;2. Institut für Anorganische Chemie, Rheinische Friedrich-Wilhelms-Universität, Gerhard-Domagk-Straße 1, D-53121 Bonn, Germany;1. The Arnold and Mabel Beckman Laboratory for Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA;2. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. (IfOK), Buchbinderstraße 5-6, D-18055, Rostock, Germany;1. Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, USA;2. Department of Medicine, Roswell Park Cancer Institute, Buffalo, NY 14263, USA;3. Department of Internal Medicine, University of Nebraska Medical Center, Omaha, NE 68198, USA;4. Department of Pharmacology, University of Iowa, Iowa City, IA 52242-1109, USA;1. Department of Pharmacology, Hoshi University School of Pharmacy and Pharmaceutical Sciences, Tokyo, 142-8501, Japan;2. Department of Toxicology, Hoshi University School of Pharmacy and Pharmaceutical Sciences, Tokyo, 142-8501, Japan;3. Institute of Drug Addiction Research, Hoshi University School of Pharmacy and Pharmaceutical Sciences, Tokyo, 142-8501, Japan;1. Sleep and Circadian Neurobiology Laboratory, Stanford University, United States;2. Department of Neuropsychiatry, Akita University Graduate School of Medicine, Japan;3. Department of Integrative Physiology, Institute of Health Biosciences, The University of Tokushima Graduate School, Japan;4. Department of Otorhinolaryngology, Jikei University School of Medicine, Japan;5. Minase Research Institute, Ono Pharmaceutical Co., Ltd., Osaka, Japan |
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| Abstract: | The first examples of the asymmetric aminohydroxylation of acryl amides are reported. This was accomplished with chiral acrylamides as substrates, which undergo diastereoselective oxidative transformation within the so-called ‘second catalytic cycle’ with diastereomeric excesses reaching 100:0. The reaction relies solely on the stereochemical information provided by the enantiomerically pure starting materials. A stereochemical model for the observed asymmetric induction is provided. |
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