Enantiomerically pure α-pinene derivatives from material of 65% enantiomeric purity. Part 2: C2-symmetric N,N′-3-(2α-hydroxy)pinane diimines and diamines |
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| Institution: | 1. Institute of Organic Chemistry, Technical University of ?ód?, 90-924 ?ód?, ?eromskiego 116, Poland;2. Institute of General and Ecological Chemistry, Technical University of ?ód?, 90-924 ?ód?, ?eromskiego 116, Poland;3. Department of Inorganic and Physical Chemistry, University of Ghent, Krijgslaan 281(S3) 9000 Ghent, Belgium;1. Department of Chemistry, School of Arts and Sciences, The Johns Hopkins University, 3400 North Charles Street, Baltimore, MD 21218, United States;2. W. Harry Feinstone Department of Molecular Microbiology and Immunology, Bloomberg School of Public Health, The Johns Hopkins University, Baltimore, MD 21205, United States;3. The Johns Hopkins Malaria Research Institute, Bloomberg School of Public Health, The Johns Hopkins University, Baltimore, MD 21205, United States;1. Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland;2. Forensic Laboratory, Internal Security Agency, 1 Sierpnia 30A, 02-134 Warsaw, Poland;3. National Medicines Institute, Che?mska 30/34, 00-725 Warsaw, Poland;4. National Centre for Nuclear Research, 05-400 Otwock-?wierk, Poland;1. Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan;2. Department of Chemistry, Faculty of Science, Ochanomizu University, 2-1-1 Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan;1. National Taras Shevchenko University of Kyiv, Volodymyrska Street 64, Kyiv 01601, Ukraine;2. Enamine Ltd, Alexandra Matrosova Street 23, Kyiv 01103, Ukraine;3. STC ‘Institute for Single Crystals’, National Academy of Sciences of Ukraine, Lenina ave. 60, 61001 Kharkiv, Ukraine;1. Steroid Research Laboratory, Department of Chemistry, Aligarh Muslim University, Aligarh 202002, UP, India;2. Department of Chemistry, Faculty of Science, King Saud University, Riyadh 11451, Saudi Arabia;3. Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, Stuttgart 70569, Germany |
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| Abstract: | The conversion of enantiomerically enriched (ee >99%) 2α-hydroxypinan-3-one and its oxime (obtained in previously described procedures1 from α-pinene of 65% ee) into a range of derivatives with potential application in asymmetric synthesis was attempted. C2-Symmetrical compounds, ligands for potential catalysts, were synthesized from 2α-hydroxypinan-3-one and either aliphatic or aromatic diamines. Reduction or etherification/reduction of selected diiminodiols afforded respective diaminodiols and diaminoethers, which were further transformed into azolium salts. Reactions of dipinanediaminoethers with dichlorophenylphosphine and subsequent in situ oxidation of the products afford the respective stable phosphinediamide oxides. Four selected compounds were crystallographically studied. |
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