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JOURNALS // Mendeleev Communications // Archive

Mendeleev Commun., 2023 Volume 33, Issue 6, Pages 762–763 (Mi mendc516)

This article is cited in 1 paper

Communications

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

A. D. Vinokurova, T. M. Iliyasova, K. A. Karpenkoa, A. V. Evstigneevaab, A. P. Minaevaa, M. N. Elinsona, A. N. Vereshchagina

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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