Asymmetric synthesis of 2-alkyl-3-thiazoline carboxylates: stereochemistry of the MnO2-mediated oxidation of cis- and trans-2-alkyl-thiazolidine-(4R)-carboxylates |
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| Institution: | 1. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky prosp. 31, 119991 Moscow, Russian Federation;2. Skobeltsyn Research Institute of Nuclear Physics, M. V. Lomonosov Moscow State University, Leninskie Gory 1/2, 119991 Moscow, Russian Federation;3. P. N. Lebedev Institute of Physics, Russian Academy of Sciences, Leninsky prosp. 53, 119991 Moscow, Russian Federation;1. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky prosp. 31, 119991 Moscow, Russian Federation;2. P. N. Lebedev Institute of Physics, Russian Academy of Sciences, Leninsky prosp. 53, 119991 Moscow, Russian Federation;3. International Tomography Center, Siberian Branch of the Russian Academy of Sciences, Institutskaya ul. 3a, 630090 Novosibirsk, Russian Federation;1. Chinese Centre for Chirality, The Key Laboratory of Medicinal Chemistry and Molecular Diagnostics of Ministry of Education, College of Pharmacy Sciences of Hebei University, Baoding, Hebei 071002, PR China;2. State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of Botany, CAS, Kunming, Yunnan 650204, PR China;1. Department of Chemistry, Oakland University, 2200 N. Squirrel Road, Rochester, MI 48309-4477, USA;2. Department of Chemistry, Eastern Illinois University, 600 Lincoln Avenue, Charleston, IL 61920-3099, USA;1. Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan;2. Department of Chemistry, Manufacturing and Control, Kobe Pharma Research Institute, Nippon Boehringer Ingelheim Co., Ltd., 6-7-5, Minatojima-minamimachi, Chuo-ku, Kobe, Hyogo 650-0047, Japan;3. Department of Pharmacokinetics and Nonclinical Safety, Kobe Pharma Research Institute, Nippon Boehringer Ingelheim Co., Ltd., 6-7-5, Minatojima-minamimachi, Chuo-ku, Kobe, Hyogo 650-0047, Japan;1. CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China;2. Shanghai Advanced Research Institute, Chinese Academy of Sciences, 99 Haike Road, Shanghai, 201210, China |
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| Abstract: | The asymmetric synthesis of a series of 3-thiazoline carboxylates, 2, was effected by MnO2 oxidation of the corresponding cis/trans thiazolidines, 1. The stereochemistry of the oxidation reaction was studied using NMR and chiral GC analyses. Compounds 2 were obtained with enantiomeric excesses (e.e.s) in the range of 40–100%. |
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