T. M. Iliyasov, K. A. Karpenko, A. D. Vinokurov, A. N. Fakhrutdinov, A. A. Tyutin, M. N. Elinson, A. N. Vereshchagin, “Highly diastereoselective multicomponent synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidineswith four and five stereogenic centers”, Mendeleev Commun., 32:5 (2022), 629

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Mendeleev Communications, 2022, Volume 32, Issue 5, Pages 629–631
DOI: https://doi.org/10.1016/j.mencom.2022.09.020 (Mi mendc748)

This article is cited in 4 scientific papers (total in 4 papers)

Communications

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

T. M. Iliyasov^a, K. A. Karpenko^a, A. D. Vinokurov^a, A. N. Fakhrutdinov^a, A. A. Tyutin^b, M. N. Elinson^a, A. N. Vereshchagin^a

^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

Full-text PDF (177 kB) Citations (4) Supplementary materials

DOI: https://doi.org/10.1016/j.mencom.2022.09.020

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

Abstract: 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.

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

Bibliographic databases:

Document Type: Article

Language: English

*Supplementary materials:*
		Supplementary_data_1.pdf	(6.0 Mb)

Citation: T. M. Iliyasov, K. A. Karpenko, A. D. Vinokurov, A. N. Fakhrutdinov, A. A. Tyutin, M. N. Elinson, A. N. Vereshchagin, “Highly diastereoselective multicomponent synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidineswith four and five stereogenic centers”, Mendeleev Commun., 32:5 (2022), 629–631

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https://www.mathnet.ru/eng/mendc/v32/i5/p629

This publication is cited in the following 4 articles:

Citing articles in Google Scholar: Russian citations, English citations
Related articles in Google Scholar: Russian articles, English articles

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