Diastereocontrol via the phenol- and palladium(II)-catalyzed Claisen rearrangement with cyclic enol ethers |
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| Affiliation: | 1. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China;2. Department of Pharmacy, Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China;1. Max Planck Institute for Chemical Energy Conversion, Stiftstrasse 34, 45470 Mülheim an der Ruhr, Germany;2. Department of Bio- and Chemical Engineering, Laboratory of Industrial Chemistry, Technical University of Dortmund, Emil-Figge-Straße 66, 44227 Dortmund, Germany;1. Modern Research Center for Traditional Chinese Medicine, Beijing University of Chinese Medicine, Beijing 100029, China;2. School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100102, China;3. Baotou Medical College, Baotou 014060, China;1. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, China;2. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China;3. Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, China |
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| Abstract: | Taking the judicious choice of either 2,6-dimethylphenol or PdCl2(RCN)2 as the catalyst, the Claisen rearrangements with the enol ethers of cyclic ketones are shown to proceed with a high level of either anti or syn diastereoselection, respectively. |
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