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Enantiomerically pure disulfides: key compounds in the kinetic resolution of chiral PIII-derivatives with stereogenic phosphorus
Institution:1. Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland;2. Laboratoire de Chimie de Coordination du CNRS, 205 Route de Narbonne, 31077 Toulouse Cedex 4, France;1. State Key Laboratory of High Performance Ceramics and Superfine Microstructures, Shanghai Institute of Ceramics, Chinese Academy of Sciences, Shanghai 200050, China;2. The Key Laboratory of Inorganic Functional Materials and Device, Shanghai Institute of Ceramics, Chinese Academy of Sciences, Shanghai 200050, China;3. University of Chinese Academy of Sciences, Beijing 100049, China;1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia;2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, 9, Akad. Lavrentiev Ave., Novosibirsk 630090, Russia;3. Novosibirsk State University (National Research University), Department of Natural Sciences, 2, Pirogova Str., Novosibirsk 630090, Russia;1. Physics Department, Faculty of Science, Kafrelsheikh University, 33516 El Gaish Street, Kafr El Sheikh, Egypt;2. Chemistry Department, Faculty of Science, Kafrelsheikh University, 33516 El Gaish Street, Kafr El Sheikh, Egypt;1. Department of Chemistry and Research Center for Smart Molecules, Rikkyo University, Nishi-Ikebukuro 3-34-1, Toshima-ku, Tokyo 171-8501, Japan;2. Division of Frontier Materials Science and Center for Advanced Interdisciplinary Research, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan
Abstract:Enantiomerically pure disulfides were reacted with various chiral PIII-derivatives with stereogenic phosphorus such as tertiary phosphines, halogenophosphines, phosphinite and phosphole under kinetic resolution conditions to afford enantiomerically enriched phosphine oxides or sulfides with ee values up to 50%. Enantiomeric excess rose to 70% under dynamic kinetic resolution conditions in the case of tert-butylphenylchlorophosphine.
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