Open Access
Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent
Vadim Filatov
1
,
Vadim E Filatov
1
,
Juliana Kuznetsova
1
,
Lada Petrovskaya
1
,
Dmitry Yuzabchuk
1
,
В. А. Тафеенко
1
,
Victor A. Tafeenko
1
,
Nikolay V. Zyk
1
,
Publication type: Journal Article
Publication date: 2021-08-26
scimago Q1
wos Q2
SJR: 0.773
CiteScore: 7.1
Impact factor: 4.3
ISSN: 24701343
PubMed ID:
34514245
General Chemistry
General Chemical Engineering
Abstract
A convenient and versatile one-pot method for synthesis of 1,3-bis-aryl spirooxindolo-β-lactams from isatin Schiff bases and substituted phenylacetic acids using ketene–imine cycloaddition reaction with TsCl for a ketene generation has been developed. The reaction procedure does not require absolute solvents and unstable starting reagents. The studied reactions lead to cis-diastereoselective β-lactam formation for all tested phenylacetic acids except 4-MeOC6H4CH2COOH. An increase of trans-diastereomers yields with increasing temperature and solvent polarity was demonstrated.
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Metrics
9
Total citations:
9
Citations from 2024:
4
(44.44%)
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GOST
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Filatov V. et al. Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent // ACS Omega. 2021. Vol. 6. No. 35. pp. 22740-22751.
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Filatov V., Filatov V. E., Kuznetsova J., Petrovskaya L., Yuzabchuk D., Тафеенко В. А., Tafeenko V. A., Zyk N. V., Beloglazkina E. K. Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent // ACS Omega. 2021. Vol. 6. No. 35. pp. 22740-22751.
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RIS
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TY - JOUR
DO - 10.1021/acsomega.1c03063
UR - https://pubs.acs.org/doi/10.1021/acsomega.1c03063
TI - Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent
T2 - ACS Omega
AU - Filatov, Vadim
AU - Filatov, Vadim E
AU - Kuznetsova, Juliana
AU - Petrovskaya, Lada
AU - Yuzabchuk, Dmitry
AU - Тафеенко, В. А.
AU - Tafeenko, Victor A.
AU - Zyk, Nikolay V.
AU - Beloglazkina, Elena K.
PY - 2021
DA - 2021/08/26
PB - American Chemical Society (ACS)
SP - 22740-22751
IS - 35
VL - 6
PMID - 34514245
SN - 2470-1343
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2021_Filatov,
author = {Vadim Filatov and Vadim E Filatov and Juliana Kuznetsova and Lada Petrovskaya and Dmitry Yuzabchuk and В. А. Тафеенко and Victor A. Tafeenko and Nikolay V. Zyk and Elena K. Beloglazkina},
title = {Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent},
journal = {ACS Omega},
year = {2021},
volume = {6},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://pubs.acs.org/doi/10.1021/acsomega.1c03063},
number = {35},
pages = {22740--22751},
doi = {10.1021/acsomega.1c03063}
}
Cite this
MLA
Copy
Filatov, Vadim, et al. “Cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent.” ACS Omega, vol. 6, no. 35, Aug. 2021, pp. 22740-22751. https://pubs.acs.org/doi/10.1021/acsomega.1c03063.
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