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ЖУРНАЛЫ // Mendeleev Communications // Архив

Mendeleev Commun., 2022, том 32, выпуск 5, страницы 629–631 (Mi mendc748)

Эта публикация цитируется в 4 статьях

Communications

Highly diastereoselective multicomponent synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidineswith four and five stereogenic centers

T. M. Iliyasova, K. A. Karpenkoa, A. D. Vinokurova, A. N. Fakhrutdinova, A. A. Tyutinb, M. N. Elinsona, A. N. Vereshchagina

a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
b D.Mendeleev University of Chemical Technology of Russia, Moscow, Russian Federation


Аннотация: The Michael–Mannich cascade cyclization of cyano olefins, ethyl 4,4,4-trifluoro-3-oxobutanoate, aromatic aldehydes and ammonium acetate provides convenient stereoselective formation of ethyl 5,5-dicyano-4,6-diaryl-2-hydroxy-2-(trifluoromethyl)piperidine-3-carboxylates with fourstereogenic centers and dialkyl 4,6-diaryl-5-cyano-2-hydroxy-2-(trifluoromethyl)piperidine-3,5-dicarboxylates with five stereogenic centers. Ammonium acetate plays dual role, acting as a base and as a nitrogen source.

Ключевые слова: multicomponent reactions, trifluoromethylpiperidines, ammonium acetate, C–H acids, stereoselectivity.

Язык публикации: английский

DOI: 10.1016/j.mencom.2022.09.020



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