Synthesis and resolution of benzylisopropylphenylphosphine,a monodentate P-chiral ligand |
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| Institution: | 1. LaMCScI, Department of Physics, 23Faculty of Sciences, University Mohammed V- Rabat, Morocco;2. Université Privée de Marrakech, Km 13, route d''Amizmiz, 42312, Marrakech, Morocco;1. Research Institute for Fragrance Materials, Inc., 50 Tice Boulevard, Woodcliff Lake, NJ, 07677, USA;2. Columbia University Medical Center, Department of Dermatology, 161 Fort Washington Ave., New York, NY, 10032, USA;3. Malmo University Hospital, Department of Occupational & Environmental Dermatology, Sodra Forstadsgatan 101, Entrance 47, Malmo, SE-20502, Sweden;4. Humphrey School of Public Affairs, University of Minnesota, 301 19th Avenue South, Minneapolis, MN, 55455, USA;5. University of Sao Paulo, School of Veterinary Medicine and Animal Science, Department of Pathology, Av. Prof. Dr. Orlando Marques de Paiva, 87, Sao Paulo, CEP 05508-900, Brazil;6. University of Wuerzburg, Department of Toxicology, Versbacher Str. 9, 97078, Würzburg, Germany;7. Oregon Health Science University, 3181 SW Sam Jackson Park Rd., Portland, OR, 97239, USA;8. Vanderbilt University School of Medicine, Department of Biochemistry, Center in Molecular Toxicology, 638 Robinson Research Building, 2200 Pierce Avenue, Nashville, TN, 37232-0146, USA;9. Department of Dermatology, Kyoto University Graduate School of Medicine, 54 Kawahara-cho, Shogoin, Sakyo-ku, Kyoto, 606-8507, Japan;10. The University of Tennessee, College of Veterinary Medicine, Department of Comparative Medicine, 2407 River Dr., Knoxville, TN, 37996-4500, USA;11. Department of Pharmacology, University of Arizona, College of Medicine, 1501 North Campbell Avenue, P.O. Box 245050, Tucson, AZ, 85724-5050, USA;1. Henan Key Laboratory of Boron Chemistry and Advanced Energy Materials, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China;2. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, China |
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| Abstract: | The synthesis of benzylisopropylphenylphosphine by reaction between the benzylphenylphosphide anion and isopropyl chloride and its subsequent resolution by means of an optically active palladium metallacycle is reported. The synthesis of the organometallic complex Pd(η3-2-MeC3H4)Cl(PBniPrPh)] is also described, as well as the assignment of the absolute configuration of the coordinated phosphine by mono- and bidimensional proton NMR spectra, using the homochiral palladacycle as a reference point. In order to estimate the height of the energy barrier corresponding to the rotation of the phosphine ligand around the PdP bond, several calculations were performed at the semiempirical PM3(tm) level. |
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