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Diastereoselective cycloaddition of isatin azomethine ylides to 5-arylidene-2-thiohydantoins bearing 3-positioned chiral substituent

Alexandr Anatol'evich Barashkin 1
Alexandr Anatol'evich Barashkin
, 
Vladislav Sergeyevich Polyakov 1
Vladislav Sergeyevich Polyakov
, 
Nikita Leonidovich Shikut 1
Nikita Leonidovich Shikut
, 
Anastasia Dmitrievna Putilova 1
Anastasia Dmitrievna Putilova
, 
Anton Rodionovich Gorovoy 1
Anton Rodionovich Gorovoy
,  , 
Victor Aleksandrovich Tafeenko 1
Victor Aleksandrovich Tafeenko
, 
Boris Nikolaevich Tarasevich 1
Boris Nikolaevich Tarasevich
, 
Nikolai Vasil'evich Zyk 1
Nikolai Vasil'evich Zyk
, 
10.1016/j.mencom.2022.03.022
Published 2022-03-06
Communication , Volume 32, Issue 2, 221-223
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Barashkin A. A. et al. Diastereoselective cycloaddition of isatin azomethine ylides to 5-arylidene-2-thiohydantoins bearing 3-positioned chiral substituent // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 221-223.
GOST all authors (up to 50) Copy
Barashkin A. A., Polyakov V. S., Shikut N. L., Putilova A. D., Gorovoy A. R., Degtiarev A. D., Tafeenko V. A., Tarasevich B. N., Zyk N. V., Beloglazkina E. K. Diastereoselective cycloaddition of isatin azomethine ylides to 5-arylidene-2-thiohydantoins bearing 3-positioned chiral substituent // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 221-223.
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TY - JOUR
DO - 10.1016/j.mencom.2022.03.022
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.022
TI - Diastereoselective cycloaddition of isatin azomethine ylides to 5-arylidene-2-thiohydantoins bearing 3-positioned chiral substituent
T2 - Mendeleev Communications
AU - Barashkin, Alexandr Anatol'evich
AU - Polyakov, Vladislav Sergeyevich
AU - Shikut, Nikita Leonidovich
AU - Putilova, Anastasia Dmitrievna
AU - Gorovoy, Anton Rodionovich
AU - Degtiarev, Anton Dmitrievich
AU - Tafeenko, Victor Aleksandrovich
AU - Tarasevich, Boris Nikolaevich
AU - Zyk, Nikolai Vasil'evich
AU - Beloglazkina, Elena Kimovna
PY - 2022
DA - 2022/03/06
PB - Mendeleev Communications
SP - 221-223
IS - 2
VL - 32
ER -
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@article{2022_Barashkin,
author = {Alexandr Anatol'evich Barashkin and Vladislav Sergeyevich Polyakov and Nikita Leonidovich Shikut and Anastasia Dmitrievna Putilova and Anton Rodionovich Gorovoy and Anton Dmitrievich Degtiarev and Victor Aleksandrovich Tafeenko and Boris Nikolaevich Tarasevich and Nikolai Vasil'evich Zyk and Elena Kimovna Beloglazkina},
title = {Diastereoselective cycloaddition of isatin azomethine ylides to 5-arylidene-2-thiohydantoins bearing 3-positioned chiral substituent},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.022},
number = {2},
pages = {221--223},
doi = {10.1016/j.mencom.2022.03.022}
}
MLA
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Barashkin, Alexandr Anatol'evich, et al. “Diastereoselective cycloaddition of isatin azomethine ylides to 5-arylidene-2-thiohydantoins bearing 3-positioned chiral substituent.” Mendeleev Communications, vol. 32, no. 2, Mar. 2022, pp. 221-223. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.022.

Keywords

azomethine ylide
chiral substituent
diastereoselectivity
isatin
spiro compound
spirooxindole
thiohydantoin

Abstract

1,3-Dipolar cycloaddition of azomethine ylide, generated from isatin and sarcosine, with 5-arylidene-2-thiohydantoins equipped with various chiral substituents at the N3 atom occurs diastereoselectively. The highest selectivity with dr = 5 : 1 was observed for the 2-thiohydantoin bearing 1,2-diphenylethyl substituent.

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