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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. 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
Full-text PDF (177 kB) Citations (4)
DOI: https://doi.org/10.1016/j.mencom.2022.09.020
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.
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
Linking options:
  • https://www.mathnet.ru/eng/mendc748
  • https://www.mathnet.ru/eng/mendc/v32/i5/p629
    • This publication is cited in the following 4 articles:
    1. A. D. Vinokurov, T. M. Iliyasov, K. A. Karpenko, A. B. Valeev, A. N. Fakhrutdinov, M. N. Elinson, A. N. Vereshchagin, “One-pot formation of six bonds: pseudo-six-component diastereoselective synthesis of pyridinium-containing piperidin-2-ones”, Russ Chem Bull, 73:5 (2024), 1261  crossref
    2. Andrey D. Vinokurov, Taygib M. Iliyasov, Kirill A. Karpenko, Radmir N. Akchurin, Yana V. Derkach, Anatoly N. Vereshchagin, “Highly diastereoselective synthesis of pyridinium-substituted piperidin-2-ones from pyridinium ylides, aldehydes, Michael acceptors, and ammonium acetate”, Chem Heterocycl Comp, 59:11-12 (2023), 778  crossref
    3. Andrey D. Vinokurov, Taygib M. Iliyasov, Kirill A. Karpenko, Yana V. Derkach, Anton A. Ryabov, Sergey V. Gorbunov, Alexander S. Goloveshkin, Anatoly N. Vereshchagin, “Highly diastereoselective multicomponent synthesis of 2-piperidone-substituted pyridinium salts with three and four stereogenic centers”, Tetrahedron, 149 (2023), 133685  crossref
    4. 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., 33:6 (2023), 762–763  mathnet  crossref
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