Unexpected reversal of the enantioselectivity using chiral quinolylmethyl- and acridininyloxazolines as ligands for asymmetric palladium-catalyzed allylic alkylation |
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| Affiliation: | 1. Dipartimento di Chimica, Università di Sassari, via Vienna 2, I-07100 Sassari, Italy;2. Dipartimento Farmaco Chimico Tossicologico, Università di Sassari, Via Muroni 23, I-07100 Sassari, Italy;1. Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China;2. Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China;1. Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Cátedra de Química Medicinal, Junín 956 PP 1113, Buenos Aires, Argentina;2. CONICET-Universidad de Buenos Aires, Instituto de la Química y Metabolismo del Fármaco (IQUIMEFA), Junín 956 SS 1113, Buenos Aires, Argentina;3. Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Química Orgánica, Junín 956 3er floor, Buenos Aires, Argentina;1. Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640, China;2. School of Materials Science and Energy Engineering, Foshan University, Foshan, China;1. Department of Chemistry, Jahangirnagar University, Savar, Dhaka 1342, Bangladesh;2. Department of Agricultural Chemistry, Sher-e-Bangla Agricultural University, Sher-e-Bangla Nagar, Dhaka 1207, Bangladesh;3. Department of Chemistry, University College London, 20 Gordon Street, London WC1H OAJ, UK;4. Department of Chemistry, King''s College London, Britannia House, 7 Trinity Street, London SE1 1DB, UK;5. Department of Chemistry, University of North Texas, 1155 Union Circle, Box 305070, Denton, TX 76203, USA;6. Inorganic Research Group, Chemical Physics, Center for Chemistry and Chemical Engineering, Lund University, Post Box 124, SE-22100, Lund, Sweden;1. Key Laboratory of Engineering Plastics, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;2. Qingdao Yikesi New Material Co., LTD, Liquan Village, Laixi, Qingdao 266604, China;3. School of Materials Science and Engineering, Beijing Institute of Fashion Technology, Beijing 100029, China;4. Faculty of Chemistry, Opole University, Oleska 48, 45-052 Opole, Poland |
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| Abstract: | New chiral quinolylmethyloxazolines and acridininyloxazolines were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate. The introduction of a benzo-fused substituent on the pyridine ring not containing the chiral backbone resulted in the switch of the expected chiral sense of enantioselection of the reaction. Enantiomeric excesses up to 78% were obtained. |
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