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New chiral monodentate phospholane ligands by highly stereoselective hydrophosphination
Institution:1. Leibniz-Institut für Katalyse an der Universität Rostock e.V., A.-Einstein-Str. 29a, 18059 Rostock, Germany;2. Kyiv Taras Shevchenko University, Volodymyrska-Str. 64, 01033 Kyiv, Ukraine;3. Institut für Chemie der Universität Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany;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. Departamento de Química, Universidad de Guanajuato, Noria Alta s/n, Guanajuato, Gto 36050, Mexico;2. Departamento de Física Aplicada, Cinvestav-Unidad Mérida, Km 6, antigua carr. a Progreso, Mérida, Yucatán 97310, Mexico;3. Instituto de Investigaciones Químicas, CSIC-Universidad de Sevilla, Avda. Américo Vespucio, 49, Isla de La Cartuja, 41092 Sevilla, Spain;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 Institute of Advanced Industrial Science and Technology (AIST), 1-1-1, Higashi, Tsukuba, Ibaraki 305-8565, Japan;2. Katayama Chemical Industries Co., Ltd, 26-22, 3-Chome, Higasinaniwa-cho, Amagasaki, Hyogo 660-0892, Japan;3. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan;1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 LingLing Road, Shanghai 200032, China;2. School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
Abstract:New chiral phospholanes 6 were prepared in both enantiomeric forms starting from l- and d-tartaric acid. The key step in the synthetic sequence is the double hydrophosphination of unsaturated chiral bis(lactone) 9 by NaPhPH(BH3). This method was used for the first time in the formation of chiral phospholanes. The structure of phospholane 6a was confirmed by X-ray crystallography. σ-Donor properties of the phospholanes were estimated by measurement of 1J(31P–77Se) coupling constants in the corresponding phosphine selenides. The new phospholanes were tested as ligands in the Rh-catalyzed enantioselective hydrogenation of functionalized standard olefins (65–92% ee).
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