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

Taygib Magomedsalamovich Iliyasov 1
Taygib Magomedsalamovich Iliyasov
, 
Kirill Anatol'evich Karpenko 1
Kirill Anatol'evich Karpenko
, 
Andrey D Vinokurov 1
Andrey D Vinokurov
, 
Artem Nikolaevich Fakhrutdinov 1
Artem Nikolaevich Fakhrutdinov
, 
Alexander A Tyutin 2
Alexander A Tyutin
,  , 
Anatoly Nikolaevich Vereshchagin 1
Anatoly Nikolaevich Vereshchagin
10.1016/j.mencom.2022.09.020
Published 2022-09-05
Communication , Volume 32, Issue 5, 629-631
5
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Iliyasov T. M. et al. Highly diastereoselective multicomponent synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidineswith four and five stereogenic centers // Mendeleev Communications. 2022. Vol. 32. No. 5. pp. 629-631.
GOST all authors (up to 50) Copy
Iliyasov T. M., Karpenko K. A., Vinokurov A. D., Fakhrutdinov A. N., Tyutin A. A., Elinson M. N., Vereshchagin A. N. Highly diastereoselective multicomponent synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidineswith four and five stereogenic centers // Mendeleev Communications. 2022. Vol. 32. No. 5. pp. 629-631.
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TY - JOUR
DO - 10.1016/j.mencom.2022.09.020
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.09.020
TI - Highly diastereoselective multicomponent synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidineswith four and five stereogenic centers
T2 - Mendeleev Communications
AU - Iliyasov, Taygib Magomedsalamovich
AU - Karpenko, Kirill Anatol'evich
AU - Vinokurov, Andrey D
AU - Fakhrutdinov, Artem Nikolaevich
AU - Tyutin, Alexander A
AU - Elinson, Michail Nikolaevich
AU - Vereshchagin, Anatoly Nikolaevich
PY - 2022
DA - 2022/09/05
PB - Mendeleev Communications
SP - 629-631
IS - 5
VL - 32
ER -
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@article{2022_Iliyasov,
author = {Taygib Magomedsalamovich Iliyasov and Kirill Anatol'evich Karpenko and Andrey D Vinokurov and Artem Nikolaevich Fakhrutdinov and Alexander A Tyutin and Michail Nikolaevich Elinson and Anatoly Nikolaevich Vereshchagin},
title = {Highly diastereoselective multicomponent synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidineswith four and five stereogenic centers},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.09.020},
number = {5},
pages = {629--631},
doi = {10.1016/j.mencom.2022.09.020}
}
MLA
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Iliyasov, Taygib Magomedsalamovich, et al. “Highly diastereoselective multicomponent synthesis of polysubstituted 2-hydroxy-2-trifluoromethylpiperidineswith four and five stereogenic centers.” Mendeleev Communications, vol. 32, no. 5, Sep. 2022, pp. 629-631. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.09.020.

Keywords

ammonium acetate
C–H acids
multicomponent reactions
stereoselectivity
trifluoromethylpiperidines

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.

References

1.
Rational design of potent sialidase-based inhibitors of influenza virus replication
von Itzstein M., Wu W., Kok G.B., Pegg M.S., Dyason J.C., Jin B., Van Phan T., Smythe M.L., White H.F., Oliver S.W., Colman P.M., Varghese J.N., Ryan D.M., Woods J.M., Bethell R.C., et. al.
Nature, 1993
2.
Influenza neuraminidase inhibitors possessing a novel hydrophobic interaction in the enzyme active site: design, synthesis, and structural analysis of carbocyclic sialic acid analogues with potent anti-influenza activity.
Kim C.U., Lew W., Williams M.A., Liu H., Zhang L., Swaminathan S., Bischofberger N., Chen M.S., Mendel D.B., Tai C.Y., Laver W.G., Stevens R.C.
Journal of the American Chemical Society, 1997
4.
Metabolomic biomarkers for personalised glucose lowering drugs treatment in type 2 diabetes
den Ouden H., Pellis L., Rutten G.E., Geerars-van Vonderen I.K., Rubingh C.M., van Ommen B., van Erk M.J., Beulens J.W.
Metabolomics, 2016
5.
10.1016/j.mencom.2022.09.020_b0025
Organofluorine Chemistry: Principles and Commercial Application, 1994
6.
10.1016/j.mencom.2022.09.020_b0030
Organic Chemistry in Medicinal Chemistry and Biochemical Applications, 1993
7.
Screening of fluorinated materials degrading microbes
Iwai N., Sakai R., Tsuchida S., Kitazume M., Kitazume T.
Journal of Fluorine Chemistry, 2009
10.
Design, Synthesis, and Mechanism of Antiviral Acylurea Derivatives Containing a Trifluoromethylpyridine Moiety
Guo S., Zhao W., Wang Y., Zhang W., Chen S., Wei P., Wu J.
Journal of Agricultural and Food Chemistry, 2021
12.
10.1016/j.mencom.2022.09.020_b0060
Multicomponent Reactions in Organic Synthesis, 2015
15.
Vereshchagin A.N., Karpenko K.A., Elinson M.N., Dorofeeva E.O., Goloveshkin A.S., Egorov M.P.
Mendeleev Communications, 2018
16.
Four-component stereoselective synthesis of tetracyano-substituted piperidines
Vereshchagin A.N., Karpenko K.A., Elinson M.N., Goloveshkin A.S., Ushakov I.E., Egorov M.P.
Research on Chemical Intermediates, 2018
17.
Highly diastereoselective four-component synthesis of polysubstituted 2-piperidinones with three and four stereogenic centers
Vereshchagin A.N., Karpenko K.A., Elinson M.N., Goloveshkin A.S., Dorofeeva E.O., Egorov M.P.
Research on Chemical Intermediates, 2019
18.
Electrocatalytic transformation of dialkyl malonates and arylidene- or alkylidenemalononitriles into dialkyl esters of 3-substituted 2,2-dicyanocyclopropane-1,1-dicarboxylic acids
Elinson M.N., Feducovich S.K., Zaimovskaya T.A., Vereshchagin A.N., Gorbunov S.V., Nikishin G.I.
Russian Chemical Bulletin, 2005
21.
Electrochemical Synthesis of Heterocycles via Cascade Reactions
Elinson M.N., Vereshchagin A.N., Ryzkov F.V.
Current Organic Chemistry, 2017
22.
Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines
Vereshchagin A.N., Iliyasov T.M., Karpenko K.A., Smirnov V.A., Ushakov I.E., Elinson M.N.
Chemistry of Heterocyclic Compounds, 2021
23.
Convenient one-pot MCRs to trifluoromethylated spiropiperidine under catalyst-free conditions
Zhou L., Yuan F., Zhou Y., Duan W., Zhang M., Deng H., Song L.
Tetrahedron, 2018
25.
Iodine catalyzed one-pot multi-component reaction to CF3-containing spiro[indene-2,3′-piperidine] derivatives
Dai B., Duan Y., Liu X., Song L., Zhang M., Cao W., Zhu S., Deng H., Shao M.
Journal of Fluorine Chemistry, 2012