New non-C2-symmetric phosphine-phosphonites as ligands in asymmetric metal catalysis |
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| Affiliation: | 1. Institute of Organic Chemistry, National Academy of Sciences of the Ukraine, Murmanskaya St., 5, UA-02094, Kyiv, Ukraine;2. Department of Chemistry, Taras Shevchenko National University of Kyiv, 64/13, Volodymyrska Str. Kyiv, 01601, Ukraine;3. The Chemours Company, 200 Powder Mill Rd., Experimental Station Wilmington, DE, 19803, USA;1. Ludwig-Maximilians-Universität Munich (LMU), Biocenter, Department of Biology II Großhaderner Str. 2, 82152, Planegg-Martinsried, Germany;2. University of Gdańsk, Faculty of Biology, Department of Invertebrate Zoology and Parasitology, Laboratory of Systematic Zoology, Wita Stwosza 59, 80-308, Gdańsk, Poland;3. State Key Laboratory of Palaeobiology and Stratigraphy, Nanjing Institute of Geology and Palaeontology and Center for Excellence in Life and Paleoenvironment, Chinese Academy of Sciences, Nanjing, 210008, China;4. Department of Earth Sciences, Natural History Museum, Cromwell Road, London, SW7 5BD, UK;1. Department of Chemistry, Philipps-Universität Marburg, Hans-Meerwein Str., 35032 Marburg, Germany;2. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany |
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| Abstract: | Starting from 1,2-dibromobenzene, the synthesis of N,N,N′,N′-tetraethyl-[2-(diphenylphosphino)phenyl]phosphonous acid tetraamide is possible in two simple steps. This key compound reacts with a variety of chiral diols such as (R)- and (S)-binaphthol, 1,2:5,6-diisopropylidene-d-mannitol or (1R,2R)-1,2-diphenyl-1,2-ethane diol to form the corresponding non-C2-symmetric phosphine-phosphonite compounds. These ligands react with Rh(COD)2BF4 to form bidentate Rh-complexes which serve as catalysts in the asymmetric hydrogenation of dimethyl itaconate with ee values of up to 88%. |
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