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Asymmetric reduction of substituted indanones and tetralones catalyzed by chiral dendrimer and its application to the synthesis of (+)-sertraline
Institution:1. Department of Chemistry, University of Nebraska Kearney, Kearney, NE, 68849, United States;2. Department of Bioengineering and Therapeutic Sciences, Schools of Pharmacy and Medicine, University of California San Francisco, San Francisco, CA 94158, United States;3. Department of Pharmacology and Systems Therapeutics; Department of Structural and Chemical Biology, Icahn School of Medicine at Mount Sinai, New York, NY 10029, United States;1. Departamento de Química Bioorgánica, Instituto de Química Orgánica General, CSIC, Calle Juan de la Cierva 3, 28006 Madrid, Spain;2. Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Biotecnología de Asturias, University of Oviedo, Avenida Julián Clavería 8, 33006 Oviedo, Spain;3. IBG-1: Biotechnology, Forschungszentrum Jülich GmbH, Wilhelm-Johnen-Strasse, 52425 Jülich, Germany;4. Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28/II, 8010 Graz, Austria;1. Department of Chemistry, University of Pannonia, H-8200 Veszprém, Hungary;2. Aix-Marseille Université, FR1739, Spectropole, Campus St. Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille cedex 20, France;1. Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China;2. Shanghai Collaborative Innovation Center for Biomanufacturing Technology, 130 Meilong Road, Shanghai 200237, China
Abstract:A recoverable dendrimeric supported prolinol was used as a catalyst in the asymmetric reduction of indanones and tetralones to give separable cis and trans isomers up to 97% ee. This method was also applied in the enantioselective synthesis of the antidepressant drug (+)-sertraline.
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