Enantiomeric impurities in chiral catalysts,auxiliaries and synthons used in enantioselective synthesis |
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| Institution: | 1. Department of Pharmaceutics, Shandong Cancer Hospital and Institute, Shandong First Medical University and Shandong Academy of Medical Sciences, Jinan 250117, China;2. Shandong Academy of Traditional Chinese Medicine, Jinan 250014, China;3. State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;4. Department of Medical Oncology, Shandong Cancer Hospital and Institute, Shandong First Medical University and Shandong Academy of Medical Sciences, Jinan 250117, China;1. Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary;2. Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, H-6720 Szeged, Hungary;3. Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019-0065, USA;1. Sanofi, LGCR Chemistry, 65926 Frankfurt am Main, Germany;2. University of Hamburg, Department of Chemistry, Pharmaceutical and Medicinal Chemistry, Bundesstraße 45, 20146 Hamburg, Germany |
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| Abstract: | Eighty three popular chiral reagents that are used to synthesize a wide variety of compounds of high enantiomeric purity were analyzed in order to determine their enantiomeric composition. Included in the study are chiral catalysts for stereoselective reductions, epoxidations and hydrocarboxylations; chiral auxiliaries including a variety of oxazolidinones; a wide variety of chiral synthons and chiral resolving agents. Enantiomeric impurities were found in all reagents. The reagents were categorized by the level of their enantiomeric contaminants. The four level ranges were: 0.01% to 0.1%, 0.1% to 1%, 1% to 10% and >10%. Over half of the chiral reagents tested had enantiomeric impurities at levels >0.1%. The batch to batch enantiopurity of a reagent from a single source was examined as well as the variation in the enantiopurity of the same reagent from different sources. Possible adverse aspects of having unknown quantities of enantiomeric impurities in stereoselective syntheses are mentioned. |
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