Water-tolerant enantioselective carbonyl-ene reactions with palladium(II) and platinum(II) Lewis acid catalysts bearing BINAP |
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| Institution: | 1. Institute of Chemical and Engineering Sciences (ICES), 1 Pesek Road, Jurong Island, Singapore 627833, Singapore;2. Institut für Chemie, Technische Universität Berlin (TU-Berlin), Straße des 17, Juni 135, D-10623 Berlin, Germany;1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany;2. Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia;1. Institute of Chemistry and Chemical Engineering, Hebei Normal University, Shijiazhuang 050091, China;2. Key Laboratory of Engineering Plastics and Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;3. Department of Chemistry, University of Hull, Hull HU6 7RX, UK;1. MTA-PTE Research Group for Selective Chemical Syntheses, Ifjúság u. 6, H-7624, Pécs, Hungary;2. Department of Inorganic Chemistry, University of Pécs and Szentágothai Research Centre, PO Box 266, H-7624, Pécs, Hungary;1. Department of Medicine, Addenbrooke''s Hospital, University of Cambridge, Cambridge CB2 0QW, UK;2. School of Medicine, Tsinghua University, Beijing, China;3. Faculty of Law, University of Cambridge, Cambridge, UK;4. Clinical Microbiology and Public Health Laboratory, Public Health England, Cambridge, UK;5. Molecular Mycobacteriology, Research Center Borstel, Borstel, Germany;6. German Centre for Infection Research, Borstel, Germany;7. Denver Public Health, Denver, USA;8. Tuberculosis Section, Centre for Infectious Disease Surveillance and Control, Public Health England, London, UK;9. Research Department of Infection and Population Health, University College London, London, UK;10. Centre for Tuberculosis, National Institute for Communicable Diseases, Johannesburg, South Africa;11. TB Centre, London School of Hygiene and Tropical Medicine, London, UK;12. Laboratorio de Investigación de Enfermedades Infecciosas, Universidad Peruana Cayetano Heredia, Lima, Peru;13. Cambridge University Hospitals NHS Foundation Trust, Cambridge, UK;14. Wellcome Trust Sanger Institute, Wellcome Trust Genome Campus, Hinxton, UK;1. Department of Chemistry, Annamalai University, Annamalainagar 608 002, India;2. Department of Physics, Annamalai University, Annamalainagar 608 002, India |
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| Abstract: | Palladium(II) and platinum(II) Lewis acid catalysts bearing BINAP have been proved to be water-tolerant in enantioselective carbonyl-ene reactions, thus arylglyoxal monohydrate could be used directly as substrate achieving good to excellent enantioselectivities as high as 95.4% e.e.. The enantioselective carbonyl-ene reactions using phenylglyoxal monohydrate as substrate with four alkenes including methylenecyclohexane, 2,3-dimethyl-1-butene, 2,4,4-trimethyl-1-pentene and alpha-methylstyrene, were investigated demonstrating comparable or even higher yields and enantioselectivities in comparison with the corresponding carbonyl-ene reactions using dry phenylglyoxal as substrate for both palladium(II)-BINAP catalyst and platinum(II)-BINAP catalyst. The palladium(II) and platinum(II)-BINAP catalyzed enantioselective carbonyl-ene reactions between 4-methylphenylglyoxal monohydrate and the four alkenes were also investigated affording enantioselectivities between 76.2% and 91.8% e.e.. A mechanism involving the coordination of arylglyoxal and 2,2-dihydroxy-1-phenylethanone with chiral catalyst was proposed to interpret the enantioselective carbonyl-ene reactions using arylglyoxal monohydrate as substrate. |
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