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Highly diastereoselective multicomponent synthesis of pyridinium-substituted piperidin-2-ones with three stereogenic centres

Andrey D Vinokurov 1
Andrey D Vinokurov
, 
Taygib Magomedsalamovich Iliyasov 1
Taygib Magomedsalamovich Iliyasov
, 
Kirill Anatol'evich Karpenko 1
Kirill Anatol'evich Karpenko
, 
Alexandra Vital'evna Evstigneeva 1, 2
Alexandra Vital'evna Evstigneeva
, 
Alexandra Pavlovna Minaeva 1
Alexandra Pavlovna Minaeva
,  , 
Anatoly Nikolaevich Vereshchagin 1
Anatoly Nikolaevich Vereshchagin
2 National Research University Higher School of Economics (HSE University), Moscow, Russian Federation
10.1016/j.mencom.2023.10.007
Published 2023-10-18
Communication , Volume 33, Issue 6, 762-763
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Vinokurov A. D. et al. Highly diastereoselective multicomponent synthesis of pyridinium-substituted piperidin-2-ones with three stereogenic centres // Mendeleev Communications. 2023. Vol. 33. No. 6. pp. 762-763.
GOST all authors (up to 50) Copy
Vinokurov A. D., Iliyasov T. M., Karpenko K. A., Evstigneeva A. V., Minaeva A. P., Elinson M. N., Vereshchagin A. N. Highly diastereoselective multicomponent synthesis of pyridinium-substituted piperidin-2-ones with three stereogenic centres // Mendeleev Communications. 2023. Vol. 33. No. 6. pp. 762-763.
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TY - JOUR
DO - 10.1016/j.mencom.2023.10.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.007
TI - Highly diastereoselective multicomponent synthesis of pyridinium-substituted piperidin-2-ones with three stereogenic centres
T2 - Mendeleev Communications
AU - Vinokurov, Andrey D
AU - Iliyasov, Taygib Magomedsalamovich
AU - Karpenko, Kirill Anatol'evich
AU - Evstigneeva, Alexandra Vital'evna
AU - Minaeva, Alexandra Pavlovna
AU - Elinson, Michail Nikolaevich
AU - Vereshchagin, Anatoly Nikolaevich
PY - 2023
DA - 2023/10/18
PB - Mendeleev Communications
SP - 762-763
IS - 6
VL - 33
ER -
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@article{2023_Vinokurov,
author = {Andrey D Vinokurov and Taygib Magomedsalamovich Iliyasov and Kirill Anatol'evich Karpenko and Alexandra Vital'evna Evstigneeva and Alexandra Pavlovna Minaeva and Michail Nikolaevich Elinson and Anatoly Nikolaevich Vereshchagin},
title = {Highly diastereoselective multicomponent synthesis of pyridinium-substituted piperidin-2-ones with three stereogenic centres},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.007},
number = {6},
pages = {762--763},
doi = {10.1016/j.mencom.2023.10.007}
}
MLA
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Vinokurov, Andrey D., et al. “Highly diastereoselective multicomponent synthesis of pyridinium-substituted piperidin-2-ones with three stereogenic centres.” Mendeleev Communications, vol. 33, no. 6, Oct. 2023, pp. 762-763. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.007.

Keywords

ammonium acetate
multicomponent reactions
piperidin-2-ones
pyridinium salts
stereoselectivity.
ylides

Abstract

The Michael-Mannich-cyclization cascade of dicyano olefins, 1-(2-alkoxy-2-oxoethyl)pyridin-1-ium halogenides, aromatic aldehydes and ammonium acetate provides convenient stereoselective formation of (4,6-diaryl-5,5-dicyano-2-oxo-piperidin-3-yl)pyridin-1-ium halogenides with three stereogenic centres. Ammonium acetate plays dual role acting as a base and as a nitrogen source.

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