Polymer supported trans-1-phenylsulfonylamino-2-isoborneolsulfonylaminocyclohexane ligand for the titanium catalyzed organozinc addition to ketones |
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| Institution: | 1. Departamento de Química Fundamental, Universidade Federal de Pernambuco, Recife, PE 50740-540, Brazil;2. Centro de Educação e Saúde, Universidade Federal de Campina Grande, Cuité, PB 58175-000, Brazil;1. Department of Chemistry, Youngstown State University, WBSH 5053, Youngstown, OH 44555, United States;2. Department of Chemistry, The Johns Hopkins University, Baltimore, MD 21218, United States;1. Beijing National Laboratory of Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;2. State Key Laboratory of Chemical Resource, College of Life Science and Technology, Beijing University of Chemical Technology, Beijing 100029, China;1. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;2. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China;3. Graduate School of Chinese Academy of Sciences, Beijing 100049, China;1. Graduate School of Life Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan;2. Department of Materials Chemistry, Faculty of Science and Technology, Ryukoku University, Otsu, Shiga 520-2194, Japan |
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| Abstract: | The catalytic enantioselective addition of different organozinc reagents, such as diethylzinc, or in situ generated phenylzinc derivatives to simple ketones was accomplished using titanium tetraisopropoxide and supported chiral ligands derived from trans-1-phenylsulfonylamino-2-isoborneolsulfonylamidocyclohexane, to give the corresponding tertiary alcohols with enantioselectivities up to >99%. A simple and efficient procedure for the synthesis of the disulfonamide monomeric ligand and the corresponding polymerization is described. |
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