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Palladium/chiral phosphine–olefin complexes: X-ray crystallographic analysis and the use in catalytic asymmetric allylic alkylation
Affiliation:1. School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China;2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China;1. Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan;2. Faculty of Science, Ibaraki University, Mito 310-8512, Japan;1. Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, PR China;2. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China;1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 LingLing Road, Shanghai 200032, China;2. School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China;1. Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055, China;2. Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095, USA;3. Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen, Guangdong 518055, China;1. School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China;2. Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China;3. Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen, China
Abstract:X-ray crystallographic studies on π-allylpalladium complexes coordinated with a chiral phosphine–olefin ligand (−)-1b demonstrate that the phosphine ligand shows a larger trans-influence than the π-bound olefin. The palladium/chiral phosphine–olefin complex efficiently catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with 96% enantioselectivity.
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