Steric effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation using chiral oxazolinylpyridines |
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Affiliation: | 1. Environmental Chemistry Department, IDAEA-CSIC, C/Jordi Girona 18-26, 08034 Barcelona, Spain;2. FCT, CIMA, University of Algarve, Campus de Gambelas, 8005-139 Faro, Portugal;1. Center for Renewable Carbon, Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio), University of Tennessee, 2506 Jacob Drive, Knoxville, TN 37996, USA;2. USDA Forest Service, Forest Operations Research, 521 Devall Drive, Auburn, AL 36849, USA;1. Novel Drug Discovery & Development, Lupin Limited (Research Park), 46A/47A Village Nande, Taluka Mulshi, Pune 412 115, India;2. Manipal College of Pharmaceutical Sciences, Manipal University, Manipal, Karnataka 567 104, India;1. NMR Research Centre, Indian Institute of Science, Bangalore 560012, India;2. Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560012, India;3. JEOL India Pvt. Ltd., New Delhi, India |
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Abstract: | Eight new chiral oxazolinylpyridines were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate. Catalytic activity and enantioselectivity were found to be highly dependent upon the steric requirement of the substituent on the pyridine ring: enantioselectivity up to 92% has been obtained. |
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