Organic Letters, volume 22, issue 8, pages 3023-3027
Regiodivergent Synthesis of Butenolide-Based α- and β-Amino Acid Derivatives via Base-Controlled Azirine Ring Expansion
Publication type: Journal Article
Publication date: 2020-03-31
Journal:
Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.2
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A method for the preparation of 5-aminobutenolides from 2-bromo-2H-azirine-2-carboxylic esters/amides with arylacetic acids has been developed. The reaction regioselectivity can be switched by a change of the basic catalyst, making it possible to prepare both butenolide-based α- and β-amino acid derivatives. The change in the regioselectivity is interpreted in terms of the stability and reactivity of the enolates formed during the SN2' substitution of the bromine in the azirine by the carboxylate ion.
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European Journal of Organic Chemistry
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Molecules
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Molecules
1 publication, 9.09%
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Citations by publishers
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
4 publications, 36.36%
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American Chemical Society (ACS)
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3 publications, 27.27%
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Elsevier
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Elsevier
2 publications, 18.18%
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Wiley
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Wiley
1 publication, 9.09%
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 9.09%
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4
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Sakharov P. A. et al. Regiodivergent Synthesis of Butenolide-Based α- and β-Amino Acid Derivatives via Base-Controlled Azirine Ring Expansion // Organic Letters. 2020. Vol. 22. No. 8. pp. 3023-3027.
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Sakharov P. A., Rostovskii N. V., Khlebnikov A. F., Novikov M. S. Regiodivergent Synthesis of Butenolide-Based α- and β-Amino Acid Derivatives via Base-Controlled Azirine Ring Expansion // Organic Letters. 2020. Vol. 22. No. 8. pp. 3023-3027.
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TY - JOUR
DO - 10.1021/acs.orglett.0c00793
UR - https://doi.org/10.1021%2Facs.orglett.0c00793
TI - Regiodivergent Synthesis of Butenolide-Based α- and β-Amino Acid Derivatives via Base-Controlled Azirine Ring Expansion
T2 - Organic Letters
AU - Sakharov, Pavel A
AU - Rostovskii, Nikolai V
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
PY - 2020
DA - 2020/03/31 00:00:00
PB - American Chemical Society (ACS)
SP - 3023-3027
IS - 8
VL - 22
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2020_Sakharov,
author = {Pavel A Sakharov and Nikolai V Rostovskii and Alexander F Khlebnikov and Mikhail S. Novikov},
title = {Regiodivergent Synthesis of Butenolide-Based α- and β-Amino Acid Derivatives via Base-Controlled Azirine Ring Expansion},
journal = {Organic Letters},
year = {2020},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021%2Facs.orglett.0c00793},
number = {8},
pages = {3023--3027},
doi = {10.1021/acs.orglett.0c00793}
}
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MLA
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Sakharov, Pavel A., et al. “Regiodivergent Synthesis of Butenolide-Based α- and β-Amino Acid Derivatives via Base-Controlled Azirine Ring Expansion.” Organic Letters, vol. 22, no. 8, Mar. 2020, pp. 3023-3027. https://doi.org/10.1021%2Facs.orglett.0c00793.