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Design and synthesis of new bidentate phosphoramidite ligands for enantioselective copper-catalyzed conjugate addition of diethylzinc to enones
Institution:1. Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium;2. Department of Chemistry, University of Namur, Rue de Bruxelles 61, Namur B-5000, Belgium;3. Laboratory of Microbiology, Parasitology and Hygiene (LMPH), University of Antwerp, Universiteitsplein 1, 2610 Wilrijk, Belgium;1. Department of Chemistry, Inorganic Chemistry Section, Jadavpur University, Kolkata 700 032, West Bengal, India;2. Dipartimento di Chimica e Farmacia, and Centro Interdisciplinare per lo Sviluppo della Ricerca Biotecnologica e per lo Studio della Biodiversita della Sardegna, Universitá di Sassari, Via Vienna 2, I-07100 Sassari, Italy;3. Departamento de Quimica Inorganica, Facultad de Química, Universidad de Santiago de Compostela, Campus Vida s/n, E-15782 Santiago de Compostela, Spain;4. Department of Chemistry, National Changhua University of Education, Changhua 50058, Taiwan;1. Center for Nonlinear Studies, Los Alamos National Laboratory, Los Alamos, NM, United States;2. Theoretical Division, Los Alamos National Laboratory, Los Alamos, NM, United States;3. Center for Integrated Nanotechnologies, Los Alamos National Laboratory, Los Alamos, NM, United States;4. Skolkovo Institute of Science and Technology, Novaya St., 100, Karakorum Building, 4th floor, Skolkovo 143025, Russian Federation;5. National Technical University of Ukraine, KPI, 37 Peremogy Avenue, Building 7, Kiev 03056, Ukraine;1. School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, PR China;2. Shandong Provincial Key Laboratory of Chemical Energy Storage and Cell Technology, School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, PR China;3. Beijing National Laboratory for Molecular Sciences, Center for Molecular Science, Institute of Chemistry, Key Laboratory of Organic Solids, Chinese Academy of Sciences, Zhongguancun Beiyijie No. 2, Beijing 100190, PR China
Abstract:Several thioaryl- and phosphino-phosphoramidite ligands have been synthesized from commercially available β-aminoalcohols. This new family of bidentate ligands are highly active in the enantioselective copper-catalyzed conjugate addition of diethylzinc to both cyclic and acyclic enones showing moderate to good enantiomeric excesses of up to 81%.
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