Palladium-catalyzed asymmetric allylic alkylation using iminophosphine ligands derived from chiral primary 1-ferrocenylalkylamines |
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| Institution: | 1. Department of Biotechnology, University of Turku, Tykistökatu 6 A 6th Floor, 20520 Turku, Finland;2. Department of Organic Chemistry, Autonomous University of Madrid, 28079 Madrid, Spain;1. Yunnan Institute of Materia Medica, Kunming 650111, China;2. Innovation and R&D Center, Yunnan Bai Yao Group, Kunming 650111, China;3. Yunnan Province Company Key Laboratory for TCM and Ethnic Drug of New Drug Creation, Kunming 650111, China;1. Department of Chemistry and Institutes of Biomedical Sciences, Fudan University, Shanghai 200433, China;2. Shanghai Key Laboratory of Functional Materials Chemistry, East China University of Science and Technology, Shanghai 200237, China;1. Tongji School of Pharmacy, Huazhong University of Science and Technology, Wuhan 430030, China;2. Department of Chemistry, Wuhan University, Wuhan 430072, China;3. Hubei Key Laboratory of Economic Forest Germplasm Improvement and Resources, Comprehensive Utilization, Huanggang Normal University, Huangzhou, China |
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| Abstract: | The palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propen-1-yl acetate 4 with dimethyl malonate in the presence of chiral iminophosphine ligands 3a–3d derived from chiral primary 1-ferrocenylalkylamines 1 and 2-(diphenylphosphino)benzaldehyde 2 was investigated. Excellent enantioselectivity (up to 97%) was achieved when ligand 3d was used. A mechanism for asymmetric induction in this reaction was proposed by theoretical modeling of the intermediate π-allylpalladium complexes. |
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