Tertiary amine-promoted enone aziridination: investigations into factors influencing enantioselective induction |
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| Institution: | 1. Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK;2. Syngenta Ltd, Jealott’s Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK;1. Department of Chemistry and Biochemistry, Miami University, Oxford, OH 45056, USA;2. Department of Pediatrics, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, Hubei Province 430030, PR China;3. Center for Childhood Cancer and Blood Diseases, The Research Institute at Nationwide Children’s Hospital, Department of Pediatrics, The Ohio State University, Columbus, OH, USA;4. Molecular, Cellular and Developmental Biology Program, The Ohio State University, Columbus, OH, USA;5. School of Chemistry and Chemical Engineering, Shandong University, Jinan, PR China;1. A. E. Favorsky Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk, 664033, Russia;2. Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA, 76000, Rouen, France;3. National Research Irkutsk State Technical University, Irkutsk, 664074, Russia;1. Medicinal and Chemical Institute, China Pharmaceutical University, Nanjing 210009, PR China;2. Department of Medicinal Chemistry, University of Florida, Gainesville, FL 32610, United States;3. State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Carcinogenesis and Intervention, China Pharmaceutical University, Nanjing 210009, PR China |
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| Abstract: | trans-N-Unsubstituted aziridines were synthesised (up to 77% ee) via a chiral tertiary amine-promoted nucleophilic aziridination of α,β-unsaturated ketones utilising in situ generated N–N ylides (aminimines). A wide range of chiral tertiary amines were synthesised and evaluated, allowing structure–activity relationships to be drawn. The most efficient promoter for asymmetric aziridination, quinine, was assessed with several enones to ascertain the effect of substrate structure on product ee, while the intermediate hydrazinium salt was characterised by X-ray crystallography. |
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