Copper-catalyzed [3 + 2]-cycloaddition of α-halonitroalkenes with azomethine ylides: facile synthesis of multisubstituted pyrrolidines and pyrroles
Vladimir A Motornov
1, 2, 3, 4, 5
,
Andrey A Tabolin
1, 2, 3, 4, 5
,
Yulia V. Nelyubina
3, 4, 5, 6, 7
,
Valentine G. Nenajdenko
5, 8, 9, 10, 11
,
Sema L. Ioffe
1, 2, 3, 4, 5
3
RUSSIAN ACADEMY OF SCIENCES
4
Moscow
5
Russia
|
9
DEPARTMENT OF CHEMISTRY
11
Moscow 119991
Publication type: Journal Article
Publication date: 2021-03-19
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
33899878
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
An efficient route for the synthesis of multifunctionalized pyrrolidines based on copper-catalyzed diastereoselective [3 + 2]-cycloaddition of nitroalkenes with azomethine ylides was developed. Novel fluorinated heterocycles - β-fluoro-β-nitropyrrolidines - were accessed via this method. The products can be prepared in good to excellent yields and with high diastereoselectivity. Subsequent transformations of pyrrolidines including oxidative aromatization into fluorinated pyrrolines and medicinally attractive β-fluoro-NH-pyrroles as well as chemoselective reduction reactions were demonstrated. Application of the developed procedures for the non-fluorinated analogues was demonstrated to lead to various β-substituted pyrrole derivatives.
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30
Total citations:
30
Citations from 2024:
16
(53.34%)
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GOST
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Motornov V. A. et al. Copper-catalyzed [3 + 2]-cycloaddition of α-halonitroalkenes with azomethine ylides: facile synthesis of multisubstituted pyrrolidines and pyrroles // Organic and Biomolecular Chemistry. 2021. Vol. 19. No. 15. pp. 3413-3427.
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Motornov V. A., Tabolin A. A., Nelyubina Y. V., Nenajdenko V. G., Ioffe S. L. Copper-catalyzed [3 + 2]-cycloaddition of α-halonitroalkenes with azomethine ylides: facile synthesis of multisubstituted pyrrolidines and pyrroles // Organic and Biomolecular Chemistry. 2021. Vol. 19. No. 15. pp. 3413-3427.
Cite this
RIS
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TY - JOUR
DO - 10.1039/d1ob00146a
UR - https://xlink.rsc.org/?DOI=D1OB00146A
TI - Copper-catalyzed [3 + 2]-cycloaddition of α-halonitroalkenes with azomethine ylides: facile synthesis of multisubstituted pyrrolidines and pyrroles
T2 - Organic and Biomolecular Chemistry
AU - Motornov, Vladimir A
AU - Tabolin, Andrey A
AU - Nelyubina, Yulia V.
AU - Nenajdenko, Valentine G.
AU - Ioffe, Sema L.
PY - 2021
DA - 2021/03/19
PB - Royal Society of Chemistry (RSC)
SP - 3413-3427
IS - 15
VL - 19
PMID - 33899878
SN - 1477-0520
SN - 1477-0539
ER -
Cite this
BibTex (up to 50 authors)
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@article{2021_Motornov,
author = {Vladimir A Motornov and Andrey A Tabolin and Yulia V. Nelyubina and Valentine G. Nenajdenko and Sema L. Ioffe},
title = {Copper-catalyzed [3 + 2]-cycloaddition of α-halonitroalkenes with azomethine ylides: facile synthesis of multisubstituted pyrrolidines and pyrroles},
journal = {Organic and Biomolecular Chemistry},
year = {2021},
volume = {19},
publisher = {Royal Society of Chemistry (RSC)},
month = {mar},
url = {https://xlink.rsc.org/?DOI=D1OB00146A},
number = {15},
pages = {3413--3427},
doi = {10.1039/d1ob00146a}
}
Cite this
MLA
Copy
Motornov, Vladimir A., et al. “Copper-catalyzed [3 + 2]-cycloaddition of α-halonitroalkenes with azomethine ylides: facile synthesis of multisubstituted pyrrolidines and pyrroles.” Organic and Biomolecular Chemistry, vol. 19, no. 15, Mar. 2021, pp. 3413-3427. https://xlink.rsc.org/?DOI=D1OB00146A.