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
Q1
Q1
SJR: 1.245
CiteScore: 9.3
Impact factor: 4.9
ISSN: 15237060, 15237052
PubMed ID:
32227960
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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GOST
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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.
GOST all authors (up to 50)
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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.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.0c00793
UR - https://pubs.acs.org/doi/10.1021/acs.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
PB - American Chemical Society (ACS)
SP - 3023-3027
IS - 8
VL - 22
PMID - 32227960
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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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://pubs.acs.org/doi/10.1021/acs.orglett.0c00793},
number = {8},
pages = {3023--3027},
doi = {10.1021/acs.orglett.0c00793}
}
Cite this
MLA
Copy
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://pubs.acs.org/doi/10.1021/acs.orglett.0c00793.