Discovery of chiral catalysts by asymmetric activation for highly enantioselective diethylzinc addition to imines: using racemic and achiral diimines as effective activators |
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| Institution: | 1. Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China;2. Graduate School of Chinese Academy of Sciences, Beijing, China;1. INQUINOA-CONICET, Instituto de Química Física, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, San Lorenzo 456, T4000CAN, Tucumán, Argentina;2. CEQUINOR, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, C. C. 962, 1900 La Plata, Argentina;3. Departamento de Ciencias Básicas, Universidad Nacional de Luján, Ruta 5 y 7, 6700 Luján, Buenos Aires, Argentina;1. Institute for Molecular Science, Myodaiji, Okazaki 444-8787, Japan;2. The Graduate University for Advanced Studies, Myodaiji, Okazaki 444-8787, Japan;3. Green Nanocatalysis Research Team, RIKEN Center for Sustainable Resource Science, Hirosawa, Wako 351-0198, Japan;4. JST-CREST and JST-ACCEL, Myodaiji, Okazaki 444-8787, Japan;1. Institute of Problems of Chemical Physics RAS, Chernogolovka, Russia;2. Institute of Solid State Physics RAS, Chernogolovka, Moscow Region, 142432, Russia |
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| Abstract: | A library of chiral zinc complexes formed in situ by the combination of achiral and racemic diimines with 3,3′-di(3,5-ditrifluoromethylphenyl)-BINOL and diethylzinc were evaluated in the asymmetric addition of diethylzinc to N-acylimines. In the presence of 10 mol % of chiral ligand 4 and racemic diimine 5, high enantioselectivities of up to 97% ee and yields of up to 96% were achieved for a wide range of aromatic imines in dichloromethane at −30 °C. |
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