Synthesis of enantiopure C1 symmetric diphosphines and phosphino-phosphonites with ortho-phenylene backbones |
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| Institution: | 1. Key Laboratory of Structure-Based Drugs Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang, PR China;2. Department of Pharmacology, Shenyang Pharmaceutical University, Shenyang, PR China;3. Benxi Institute of Pharmaceutical Research, Shenyang Pharmaceutical University, Shenyang, PR China;1. Laboratory of Experimental Toxicology, Department of Clinical and Toxicological Analyses, School of Pharmaceutical Sciences, University of São Paulo, São Paulo, Brazil;2. Department of Chemistry, Federal University of Pernambuco, Pernambuco, Recife, Brazil;1. School of Materials Science and Engineering, Jiangsu Collaboration Innovation Center of Photovoltaic Science and Engineering, Changzhou University, Changzhou, 213164, China;2. College of Chemistry, Key Lab of Environment-Friendly Chemistry and Application in Ministry of Education, Xiangtan University, Xiangtan, 411105, China;3. Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, 266101, China;1. Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Cátedra de Química Medicinal, Junín 956 PP 1113, Buenos Aires, Argentina;2. CONICET-Universidad de Buenos Aires, Instituto de la Química y Metabolismo del Fármaco (IQUIMEFA), Junín 956 SS 1113, Buenos Aires, Argentina;3. Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Química Orgánica, Junín 956 3er floor, Buenos Aires, Argentina;1. Department of Chemistry, Jahangirnagar University, Savar, Dhaka 1342, Bangladesh;2. Department of Agricultural Chemistry, Sher-e-Bangla Agricultural University, Sher-e-Bangla Nagar, Dhaka 1207, Bangladesh;3. Department of Chemistry, University College London, 20 Gordon Street, London WC1H OAJ, UK;4. Department of Chemistry, King''s College London, Britannia House, 7 Trinity Street, London SE1 1DB, UK;5. Department of Chemistry, University of North Texas, 1155 Union Circle, Box 305070, Denton, TX 76203, USA;6. Inorganic Research Group, Chemical Physics, Center for Chemistry and Chemical Engineering, Lund University, Post Box 124, SE-22100, Lund, Sweden |
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| Abstract: | Reaction of 2-(diphenylphosphino)phenylphosphonous acid tetramethyldiamide 1 with (+)-menthol, (1S,2S,3S,5R)-isopinocampheol and (1R,2R)-trans-cyclohexanediol affords enantiopure phosphino-phosphonite ligands 3–5. The X-ray structures of 1 (space group P21/n) and 3 (space group P21) have been determined. The reaction of 1 with (1R,2R,3S,5R)-(−)-pinanediol proceeds diastereoselectively to afford a novel type of enantiopure phosphino-phosphonite ligand 6 with an asymmetric substituted P atom. On reaction of (+)-cedryl alcohol with 1 the adduct 7 of the phosphonous acid 2-Ph2PC6H4P(O)(H)OH 9 and its dimethylammonium salt is formed through elimination of water and subsequent hydrolysis. The structure of 7 (space group P1̄) was elucidated by X-ray structural analysis. Reduction of the chlorophosphine 8 with LiAlH4 yields the novel primary–tertiary phosphine 10, which is a valuable starting material for the synthesis of the enantiopure C1 symmetric bidentate phospholane ligands 11 and 12. |
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