Furanoside thioether–phosphinite ligands for Rh-catalyzed asymmetric hydrosilylation of ketones |
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| Institution: | 1. Université de Versailles Saint Quentin-en-Yvelines, Institut Lavoisier de Versailles—UMR CNRS 8180, 45, avenue des Etats-Unis, 78035 Versailles, France;2. Université de Tunis El Manar, Faculté des Sciences de Tunis, Laboratoire de synthèse Organique et Hétérocyclique, 2092 Tunis, Tunisia;1. Ru?er Bo?kovi? Institute, Department of Physical Chemistry, Laboratory for Synthesis and Processes of Self-assembling of Organic Molecules, Bijeni?ka c. 54, P.O. Box 180, HR-10002 Zagreb, Croatia;2. Division for Materials Physics, Ru?er Bo?kovi? Institute, POB 180, HR-10002 Zagreb, Croatia;3. Department of Physics, Faculty of Science, University of Zagreb, Bijeni?ka cesta 32, HR-10000 Zagreb, Croatia;1. Chemistry Department, Saint-Petersburg State University, Universitetsky prosp. 26, St-Petersburg 198504, Russian Federation;2. Saint-Petersburg Academic University—Nanotechnology Research and Education Centre RAS, Khlopin Str. 8/3, St-Petersburg 194021, Russian Federation;1. Department of Chemistry, Tsinghua University, Beijing 100084, China;2. Institute of Chemical Materials, CAEP, Mianyang 621900, China |
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| Abstract: | A series of thioether–phosphinite ligands, easily prepared in a few steps from inexpensive d-(+)-xylose, were tested in the Rh-catalyzed hydrosilylation of ketones. Systematic variation of the electronic and steric properties of the thioether moiety provided useful information about the ligand parameters which control enantiodiscrimination. The results show that the enantiomeric excesses are strongly dependent on the steric properties of the substituent on the thioether moiety and on the steric properties of the substrate. High activities and good enantiomeric excesses (up to 90%) were obtained in the hydrosilylation of several aryl ketones. |
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