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New chiral phosphine-phosphonites derived from (2R,3R)-dimethyl tartrate, (S)-binaphthol and (1R,2S)-ephedrine
Institution:1. Institute of Nanoscience of Aragon (INA), Department of Chemical and Environmental Engineering, University of Zaragoza, 50009 Zaragoza, Spain;2. Institute of Chemical and Engineering Sciences, 1 Pesek Road, Jurong Island, Singapore 627833, Singapore;3. Department of Chemical and Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, Singapore 117576, Singapore;1. Institute of Inorganic Chemistry, Karlsruhe Institute of Technology (KIT), Engesserstraße 15, 76131 Karlsruhe, Germany;2. Institute of Physical Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber Weg 2, 76131 Karlsruhe, Germany;3. Institut für Nanotechnologie Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76021 Karlsruhe, Germany;4. Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg, 6, 76131 Karlsruhe, Germany;5. Institut für Organische Chemie, Universität Paderborn, Warburger Str. 100, 33098 Paderborn, Germany;1. Computer Science Department, Indiana University, Bloomington, 47405, IN, USA;2. Computer Engineering Department, Siirt University, 56100, Siirt, Turkey;3. Department of Electronics and Automation, K?r?ehir Ahi Evran University, 40100, K?r?ehir, Turkey;1. Materials and Manufacturing Directorate, Air Force Research Laboratory, Wright-Patterson AFB, OH 45433, USA;2. UES Inc., Dayton, OH 45432, USA;3. National Research Council, Washington, DC 20001, USA;4. University of Dayton Research Institute, Dayton, OH 45469, USA
Abstract:The reaction of 2-lithiophenyldiphenylphosphine with phosphorus trichloride afforded the new unsymmetric phosphine, dichloro(2-diphenylphosphinophenyl)phosphine (4). Condensation of 4 with (a) (2R,3R)-dimethyl tartrate or (b) (S)-binaphthol in the presence of triethylamine gave new chiral phosphine-phosphonite ligands, (2R,3R)-2-(2′-(diphenylphosphino)phenyl)-4,5-bis(carbomethoxy)-1,3,2-dioxaphospholane] ((2R,3R)-5) and (S)-2-(diphenylphosphino)benzene]1,1′-binaphthalen-2,2′-diyl]phosphonite] ((S)-6). The analogous reaction of 4 with (1R,2S)-ephedrine using N-methylmorpholine as the base, gave 2-(2′-(diphenylphosphino)phenyl)-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine] (7) as a 95:5 mixture of diastereoisomers.
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