Electrocatalytic cascade multicomponent assembling: stereoselective one-pot synthesis of the substituted 3-azabicyclo[3.1.0]hexane-1-carboxylate system from aldehyde, malononitrile, malonate and methanol |
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| Authors: | Anatolii N. Vereshchagin Tatiana A. Zaimovskaya |
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| Affiliation: | a N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russia
b A. V. Topchiev Institute of Petrochemical Synthesis, Leninsky prospect 29, 119991 Moscow, Russia |
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| Abstract: | Electrolysis of aromatic aldehydes, malononitrile and malonate in methanol in an undivided cell in the presence of sodium bromide-sodium methoxide as double mediatory system results in the stereoselective formation of methyl (1R∗,5R∗,6R∗) 6-substituted 5-cyano-4,4-dialkoxy-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylates in 50-70% yields. |
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| Keywords: | Electrolysis Electrocatalysis Stereoselectivity Cascade transformation Mediators Bicyclic pyrrolidones |
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