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Stereoselective epoxidation of 4-fluoro-4-nitrocyclohexenes
Institution:1. Department of Materials Science, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;2. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;1. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;2. Department of Biology, M. V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation;3. Federal Research Centre ‘Fundamentals of Biotechnology’ of the Russian Academy of Sciences, 119071 Moscow, Russian Federation;1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation;2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russian Federation
Abstract:Novel fluorinated α-epoxycyclohexanes were synthesized in up to 96% yields by epoxidation of the Diels–Alder adducts of β-fluoro-β-nitrostyrenes and 2,3-dimethylbuta-1,3-diene. The epoxidation with m-chloroperoxybenzoic acid and subsequent hydrolysis into diols were found to proceed in a highly stereoselective manner.
Keywords:organofluorine compounds  nitrostyrenes  Diels–Alder reaction  epoxidation  ring-opening  hydrolysis  diols
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