Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2′-pyrrolidines]
Andrey A Akaev
1
,
Victor G Desyatkin
1
,
Nataliya S Vorobyeva
3
,
Alexander G. Majouga
1, 3, 4
,
Mikhail Ya Melnikov
1
,
Publication type: Journal Article
Publication date: 2019-02-08
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
30735387
Organic Chemistry
Abstract
A novel stereocontrolled assembly of spiro[oxindole-3,2'-pyrrolidines] via [3+2]-cycloaddition of donor-acceptor cyclopropanes to electron-poor ketimines, iminooxindoles, was developed. The method allows for efficient employment of common readily available donor-acceptor cyclopropanes, functionalized with ester, keto, nitro, cyano etc. groups, and N-unprotected iminooxindoles. The stereospecificity of the initial SN2-like imine attack on a cyclopropane molecule together with a high diastereoselectivity of further C-C bond formation facilitate a rapid access to spiro[oxindole-3,2'-pyrrolidines] in their optically active forms. Preliminary in vitro testing of the synthesized compounds against LNCaP (p53+) and PC-3 (p53-) cells revealed good antiproliferative activities and p53-selectivity indices for several compounds that are intriguing in terms of their further investigation as inhibitors of MDM2-p53 interaction.
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Total citations:
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Citations from 2024:
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(19%)
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GOST
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Akaev A. A. et al. Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2′-pyrrolidines] // Journal of Organic Chemistry. 2019. Vol. 84. No. 6. pp. 3340-3356.
GOST all authors (up to 50)
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Akaev A. A., Bezzubov S. I., Desyatkin V. G., Vorobyeva N. S., Majouga A. G., Melnikov M. Y., Melnikov M. Ya., Budynina E. M. Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2′-pyrrolidines] // Journal of Organic Chemistry. 2019. Vol. 84. No. 6. pp. 3340-3356.
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TY - JOUR
DO - 10.1021/acs.joc.8b03208
UR - https://pubs.acs.org/doi/10.1021/acs.joc.8b03208
TI - Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2′-pyrrolidines]
T2 - Journal of Organic Chemistry
AU - Akaev, Andrey A
AU - Bezzubov, Stanislav I.
AU - Desyatkin, Victor G
AU - Vorobyeva, Nataliya S
AU - Majouga, Alexander G.
AU - Melnikov, Mikhail Y.
AU - Melnikov, Mikhail Ya
AU - Budynina, Ekaterina M
PY - 2019
DA - 2019/02/08
PB - American Chemical Society (ACS)
SP - 3340-3356
IS - 6
VL - 84
PMID - 30735387
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2019_Akaev,
author = {Andrey A Akaev and Stanislav I. Bezzubov and Victor G Desyatkin and Nataliya S Vorobyeva and Alexander G. Majouga and Mikhail Y. Melnikov and Mikhail Ya Melnikov and Ekaterina M Budynina},
title = {Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2′-pyrrolidines]},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.8b03208},
number = {6},
pages = {3340--3356},
doi = {10.1021/acs.joc.8b03208}
}
Cite this
MLA
Copy
Akaev, Andrey A., et al. “Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2′-pyrrolidines].” Journal of Organic Chemistry, vol. 84, no. 6, Feb. 2019, pp. 3340-3356. https://pubs.acs.org/doi/10.1021/acs.joc.8b03208.