Enantioselective addition of organolithium reagents to imines mediated by C2-symmetric bis(aziridine) ligands |
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| Affiliation: | 1. Department of Organic Chemistry, University of Uppsala Box 531, S-751 21 Uppsala, Sweden;2. Department of Organic Chemistry, The Technical University of Denmark Building 201, DK-2800 Lyngby, Denmark;1. Department of Pediatric Neurology, Capital Institute of Pediatrics, Beijing, China;2. National Key Laboratory of Cognitive Neuroscience and Learning, Institute of Cognitive Neuroscience and Learning, Beijing Normal University, Beijing, China;1. Department of Chemistry, Faculty of Science, Imam Khomeini International University, 34148-96818 Qazvin, Iran;2. Department of Chemistry, Faculty of Science, University of Zanjan, 45371-38791 Zanjan, Iran;3. Department of Crystallochemistry and Biocrystallography, Faculty of Chemistry, Nicolaus Copernicus University in Torun, 87-100 Torun, Poland;1. Institute of Molecular and Cellular Biosciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan;2. Division of Biochemistry, Department of Biomedical Sciences, Nihon University School of Medicine, Itabashi-ku, Tokyo 173-8610, Japan;1. Department of Chemistry, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, People’s Republic of China;2. School of Environment and Civil Engineering, Dongguan University of Technology, Dongguan 523808, People’s Republic of China;1. Department of Chemistry, Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, Serbia;2. Faculty of Medicine, University of Niš, Dr Zoran Ðinđić Boulevard 81, 18000 Niš, Serbia;3. Department of Physiology, Faculty of Medicine, University of Niš, Dr Zoran Ðinđić Boulevard 81, 18000 Niš, Serbia |
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| Abstract: | The C2-symmetric bis(aziridine) ligands 1–5 have been screened in the enantioselective addition of organolithium reagents to imines. Ligand 1 (used in stoichiometric amounts) was found to be superior in terms of chemical yield and enantioselectivity, the best result being 90% yield and 89% e.e. in the addition of vinyllithium to imine 6a. Use of ligand 1 in substoichiometric amounts gave poorer yield and lower enantioselectivity. The enantioselectivity of the reaction was investigated as a function of substrate, reagent, stoichiometry and temperature, but no firm mechanistic conclusions could be drawn. Preliminary results with deuterium-labelled methyllithium indicate complexation/exchange processes involving ligand, reagent and substrate. |
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