Binuclear versus mononuclear copper complexes as catalysts for asymmetric cyclopropanation of styrene |
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| Institution: | 166121. Department of Chemistry, the University of Illinois at Chicago, Chicago, Illinois 60607, USA;1. State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China;2. Collaborative Innovation Center of Atmospheric Environment and Equipment Technology, Jiangsu Key Laboratory of Atmospheric Environment Monitoring and Pollution Control (AEMPC), Nanjing University of Information Science & Technology, Nanjing, 210044, China;1. Departamento de Química, Área de Catálisis, Grupo ECOCATAL, Universidad Autónoma Metropolitana-Iztapalapa, Avenida San Rafael Atlixco # 189, 09340 Ciudad de México, Mexico;2. Instituto de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Circuito Exterior, Coyoacán, 04510 Ciudad de México, Mexico;3. Centro de Investigaciones Químicas, Instituto de Investigación en Ciencias Básicas y Aplicadas, Universidad Autónoma del Estado de Morelos, Avenida Universidad # 1001, Chamilpa, CP 62209 Cuernavaca, Morelos, Mexico;1. School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, PR China;2. Shandong Key Laboratory of Life-Organic Analysis, Key Laboratory of Pharmaceutical Intermediates and Analysis of Natural Medicine, Qufu 273165, PR China;1. Central Electrochemical Research Institute, Karaikudi 630 003, India;2. Vivekanandha Arts and Science College for Women, Veerachipalayam, Sankari (t.k), Salem District 637303, India;1. Departamento de Química, Área de Catálisis, Grupo ECOCATAL, Universidad Autónoma Metropolitana-Iztapalapa, Avenida San Rafael Atlixco # 189, 09340, Ciudad de México, Mexico;2. Instituto de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Circuito Exterior, Coyoacán, 04510, Ciudad de México, Mexico;3. Centro de Investigaciones Químicas, Instituto de Investigación en Ciencias Básicas y Aplicadas, Universidad Autónoma del Estado de Morelos, Avenida Universidad # 1001, Chamilpa, CP 62209 Cuernavaca, Morelos, Mexico;1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71467–13565, Iran;2. Department of Chemistry, Shiraz Branch, Islamic Azad University, Shiraz 71993–37635, Iran;3. Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89b, Poznan 61–614, Poland |
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| Abstract: | A number of (S)-(−)-2-amino-1,1-diaryl-1-propanol compounds have been synthesized. They were used to form the binuclear copper complexes through a spontaneous assembly of the individual components, the β-aminoalcohol, 2-hydroxy-5-methyl-1,3-benzenedialdehyde, and copper acetate monohydrate, in methanol. These binuclear complexes were examined as asymmetric catalysts for cyclopropanation of styrene by ethyl diazoacetate. Moderate improvement in enantioselectivity has been observed for the binuclear versus mononuclear copper complexes. The e.e. values up to 87% for trans and 93% for cis products and the ratio between trans and cis products up to 9:1 have been obtained. |
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