Highly diastereoselective multicomponent synthesis of 2-piperidone-substituted pyridinium salts with three and four stereogenic centers

Highly diastereoselective multicomponent synthesis of 2-piperidone-substituted pyridinium salts with three and four stereogenic centers Full article

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2023, Volume: 149, Article number : 133685, Pages count : DOI: 10.1016/j.tet.2023.133685

Authors

Vinokurov Andrey D. ¹ , Iliyasov Taygib M. ¹ , Karpenko Kirill A. ¹ , Derkach Yana V. ^2,1 , Ryabov Anton A. ^2,1 , Gorbunov Sergey V. ¹ , Goloveshkin Alexander S. ³ , Vereshchagin Anatoly N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, Moscow, Russian Federation 119334
2	Mendeleev University of Chemical Technology of Russia, Miusskaya Square 9, Moscow, Russian Federation 125047
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Vaviliva Str., 28, Moscow, Russian Federation 119334

A novel four-component (five-molecular) diastereoselective synthesis of pyridinium salts of 2-piperidinones is reported. The Knoevenagel–Michael–Mannich cascade of reactions of aromatic aldehydes (2 eq.), nitriles, pyridinium ylides and ammonium acetate in ethanol provides convenient access to 1-((3R*,4S*,6R*)-5,5-dicyano-2-oxo-4,6-diarylpiperidin-3-yl)pyridin-1-ium halogenides with three stereocenters (55–85 % yields) or 1-(3R*,4S*,5S*,6R*)-(5-cyano-5-(alkoxycarbonyl)-2-oxo-4,6-diarylpiperidin-3-yl)pyridin-1-ium halogenides with four stereocenters (56–84 % yields).

Vinokurov A.D. , Iliyasov T.M. , Karpenko K.A. , Derkach Y.V. , Ryabov A.A. , Gorbunov S.V. , Goloveshkin A.S. , Vereshchagin A.N.
Highly diastereoselective multicomponent synthesis of 2-piperidone-substituted pyridinium salts with three and four stereogenic centers
Tetrahedron. 2023. V.149. 133685 . DOI: 10.1016/j.tet.2023.133685 WOS Scopus OpenAlex

Web of science:	WOS:001101264200001
Scopus:	2-s2.0-85175448401
OpenAlex:	W4387641591

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