A. D. Vinokurov, T. M. Iliyasov, K. A. Karpenko, A. V. Evstigneeva, A. P. Minaeva, M. N. Elinson, A. N. Vereshchagin, “Highly diastereoselective multicomponent synthesis of pyridinium-substituted piperidin-2-ones with three stereogenic centres”, Mendeleev Commun., 2023, Volume 33, Issue 6,Pages <nobr>762

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Communications

Highly diastereoselective multicomponent synthesis of pyridinium-substituted piperidin-2-ones with three stereogenic centres

A. D. Vinokurov^a, T. M. Iliyasov^a, K. A. Karpenko^a, A. V. Evstigneeva^ab, A. P. Minaeva^a, M. N. Elinson^a, A. N. Vereshchagin^a

^a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^b National Research University Higher School of Economics (HSE University), Moscow, Russian Federation

Abstract: The Michael–Mannich–cyclization cascade of dicyano olefins, 1-(2-alkoxy-2-oxoethyl)pyridin-1-ium halogenides, aromatic aldehydes and ammonium acetate provides convenient stereoselective formation of (4,6-diaryl-5,5-dicyano-2-oxo-piperidin-3-yl)pyridin-1-ium halogenides with three stereogenic centres. Ammonium acetate plays dual role acting as a base and as a nitrogen source.

Keywords: multicomponent reactions, ylides, pyridinium salts, piperidin-2-ones, ammonium acetate, stereoselectivity.

Language: English

DOI: 10.1016/j.mencom.2023.10.007

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