Limonene oxide derived aziridinyl alcohols as highly efficient catalysts for asymmetric additions of organozinc species to aldehydes |
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| Affiliation: | 1. Fukushima Environmental Safety Center, Headquarters of Fukushima Partnership Operations, Japan Atomic Energy Agency, 7th Floor, NBF-Unix Building, 6-6 Sakae-machi, Fukushima 960-8031, Japan;2. Materials Science Research Division, Quantum Beam Science Directorate, Japan Atomic Energy Agency, 2-4 Shirakata-Shirane, Tokai-mura, Ibaraki 319-1195, Japan;1. University Sidi Mohamed Ben Abdellah, Faculty of Sciences Dhar el Mahraz, Laboratory of Solid State Physics, Research Group Polymers and Nanomaterials, P.O. Box 1796, Atlas Fez 30 000, Morocco;2. iThemba LABS–National Research Foundation of South Africa, Old Faure Road, P.O. Box 722, Somerset West 7129, Western Cape Province, South Africa;3. UNESCO–UNISA Africa Chair in Nanosciences–Nanotechnology, College of Graduate Studies, University of South Africa, Muckleneuk Ridge, P.O. Box 392, Pretoria, South Africa;1. Laboratori de Química Farmacèutica (Unitat Associada al CSIC), Facultat de Farmàcia, and Institute of Biomedicine (IBUB), Universitat de Barcelona, Av. Joan XXIII, s/n, Barcelona E-08028, Spain;2. Departament de Fisicoquímica, Facultat de Farmàcia and Institute of Biomedicine (IBUB), Universitat de Barcelona, Av. Prat de la Riba, 171, 08921 Santa Coloma de Gramenet, Spain;3. Endocrinology Unit, Centre for Cardiovascular Science, University of Edinburgh, Queen’s Medical Research Institute, EH16 4TJ, United Kingdom;1. Atkins North America, Inc., 2001 NW 107 Avenue, Doral, FL 33172, USA;2. AMEC Environment and Infrastructure, Inc., 3800 Ezell Road, Suite 100, Nashville, TN 37211, USA;3. Bureau of Safety and Environmental Enforcement, 1201 Elmwood Park Boulevard, New Orleans, LA 70123, USA;4. Bureau of Ocean Energy Management, 1201 Elmwood Park Boulevard, New Orleans, LA 70123, USA;1. State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, PR China;2. Laboratory of Green Chemistry and Process, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, PR China;3. University of Chinese Academy of Sciences, Beijing 100049, PR China;1. Department of Applied Chemistry, Faculty of Science, Tokyo University of Science , 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan;2. Photocatalysis International Research Center, Research Institute for Science and Technology, Tokyo University of Science , 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan |
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| Abstract: | ![]()
The facile synthesis of a series of novel catalysts bearing a tertiary hydroxyl group and an aziridine moiety as chelating centers constructed on the scaffold derived from limonene oxide is described. The newly prepared compounds have been tested for the enantioselective addition of diethylzinc and phenylethynylzinc to aryl and alkyl aldehydes, affording the corresponding chiral alcohols in very high chemical yields (up to 96%) and with excellent ee’s of ca. 95%. |
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