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Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols

Viktoria Alekseevna Ikonnikova 1, 2
Viktoria Alekseevna Ikonnikova
, 
Ekaterina Andreevna Zhigileva 1, 3
Ekaterina Andreevna Zhigileva
, 
Andrei V Kuleshov 1, 3
Andrei V Kuleshov
, 
Vasilisa V Shirokova 1, 2
Vasilisa V Shirokova
, 
Mikhail S. Baranov 1
Mikhail S. Baranov
, 
Andrey Andreevich Mikhaylov 1
Andrey Andreevich Mikhaylov
10.1016/j.mencom.2021.09.021
Published 2021-09-08
Communication , Volume 31, Issue 5, 657-658
5
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Ikonnikova V. A. et al. Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 657-658.
GOST all authors (up to 50) Copy
Ikonnikova V. A., Zhigileva E. A., Kuleshov A. V., Shirokova V. V., Baranov M. S., Mikhaylov A. A. Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 657-658.
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TY - JOUR
DO - 10.1016/j.mencom.2021.09.021
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.021
TI - Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols
T2 - Mendeleev Communications
AU - Ikonnikova, Viktoria Alekseevna
AU - Zhigileva, Ekaterina Andreevna
AU - Kuleshov, Andrei V
AU - Shirokova, Vasilisa V
AU - Baranov, Mikhail S.
AU - Mikhaylov, Andrey Andreevich
PY - 2021
DA - 2021/09/08
PB - Mendeleev Communications
SP - 657-658
IS - 5
VL - 31
ER -
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@article{2021_Ikonnikova,
author = {Viktoria Alekseevna Ikonnikova and Ekaterina Andreevna Zhigileva and Andrei V Kuleshov and Vasilisa V Shirokova and Mikhail S. Baranov and Andrey Andreevich Mikhaylov},
title = {Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.021},
number = {5},
pages = {657--658},
doi = {10.1016/j.mencom.2021.09.021}
}
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Ikonnikova, Viktoria Alekseevna, et al. “Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols.” Mendeleev Communications, vol. 31, no. 5, Sep. 2021, pp. 657-658. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.021.

Keywords

alcohols
donor–acceptor cyclopropanes
imidazolones
nucleophilic ring opening
spirocyclic compounds

Abstract

Imidazolone-activated donor–acceptor cyclopropanes undergo alcohol-assisted ring opening under the co-action of p-toluenesulfonic acid. Under the optimized conditions, cyclopropanes and alcohols are coupled in 1,3-fashion with the retention of heterocyclic fragment. Substrates with aromatic donor groups provide the addition products in 75–99% yields as mixtures of two diastereomers.

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