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Synthesis of unsaturated silyl nitronates via the silylation of conjugated nitroalkenes
Authors:Elizaveta A. Khotyantseva  Andrey A. Tabolin  Roman A. Novikov  Yulia V. Nelyubina  Sema L. Ioffe
Affiliation:1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 47, Moscow 119991, Russia;2. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991, Russia;3. V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov Str. 32, Moscow 119991, Russia;4. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, Moscow 119991, Russia
Abstract:A new method for the synthesis of conjugated silyl nitronates from nitroalkenes is described. The procedure has wide substrate scope and is compatible with in situ generation of the substrates from 2-nitroalcohols or 2-chloro-nitroalkanes. A cascade transformation to give 3,4,5,6-tetrahydropyridine N-oxide derivatives was disclosed.
Keywords:Silyl nitronates  Nitro compounds  One pot reactions  [5+2]-Cycloaddition  Michael addition
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