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Zinc-mediated asymmetric epoxidation of nitro alkenes with oxygen
Institution:1. The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA, Molecule Structure Research Centre, 26 Azatutyan Av., Yerevan 0014, Armenia;2. Lake Superior State University, Department of Chemistry, 650 W. Easterday Ave., Sault Ste, Marie, MI 49783, USA;1. V.I. Vernadskii Institute of General and Inorganic Chemistry NAS of Ukraine, Palladin Ave. 32/34, 03680 Kyiv, Ukraine;2. Department of Inorganic Chemistry, Dresden University of Technology, Bergstrasse 66, 01069 Dresden, Germany;3. Educational and Scientific Centre “Institute of Biology” of Taras Shevchencko National University, Glushkov Ave. 2, 03022 Kyiv, Ukraine;4. Institute of Organic Chemistry NAS of Ukraine, Murmanska Str. 5, 02660 Kyiv, Ukraine;5. National Cancer Institute, Lomonosov Str. 33/43, 03022 Kyiv, Ukraine;1. Department of Chemistry, Kyungpook National University, Daegu 41566, Republic of Korea;2. Department of Fine Chemistry, Seoul National University of Science and Technology, Seoul 01811, Republic of Korea;3. Department of Chemistry Education, Kyungpook National University, Daegu 41566, Republic of Korea;1. A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 119991 Moscow, Russian Federation;2. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;3. G. V. Plekhanov Russian University of Economics, 117997 Moscow, Russian Federation;1. Department of Chemistry, University of Zanjan, 45195-313, Zanjan, Islamic Republic of Iran;2. Institute of Physics, Polish Academy of Sciences (PAN), Al. Lotnikow 32/46, PL-02-668 Warsaw, Poland
Abstract:The asymmetric epoxidation of nitro alkenes using oxygen in the presence of diethylzinc and N-methyl pseudo-ephedrine as a chiral additive is reported. This method provides an access to 3-substituted trans-2-nitro oxiranes of excellent diastereomeric purity (de≥98%) and with medium to good enantiomeric excesses (ee=36–82%).
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