Cu(I)-NHC-Catalyzed (2 + 3)-Annulation of Tetramic Acids with 2H-Azirines: Stereoselective Synthesis of Functionalized Hexahydropyrrolo[3,4-b]pyrroles
Publication type: Journal Article
Publication date: 2015-08-14
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
26271187
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A stereoselective and high-yield synthesis of hexahydropyrrolo[3,4-b]pyrroles from tetramic acids and 2H-azirines under Cu(I)-NHC catalysis is developed. An unusual N-C2 azirine bond cleavage, initiated by a copper enolate, was rationalized in terms of a free radical reaction mechanism.
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Total citations:
43
Citations from 2024:
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(11%)
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Rostovskii N. V. et al. Cu(I)-NHC-Catalyzed (2 + 3)-Annulation of Tetramic Acids with 2H-Azirines: Stereoselective Synthesis of Functionalized Hexahydropyrrolo[3,4-b]pyrroles // Organic Letters. 2015. Vol. 17. No. 17. pp. 4148-4151.
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Rostovskii N. V., Sakharov P. A., Novikov M. S., Khlebnikov A. F., Starova G. L. Cu(I)-NHC-Catalyzed (2 + 3)-Annulation of Tetramic Acids with 2H-Azirines: Stereoselective Synthesis of Functionalized Hexahydropyrrolo[3,4-b]pyrroles // Organic Letters. 2015. Vol. 17. No. 17. pp. 4148-4151.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.orglett.5b01883
UR - https://doi.org/10.1021/acs.orglett.5b01883
TI - Cu(I)-NHC-Catalyzed (2 + 3)-Annulation of Tetramic Acids with 2H-Azirines: Stereoselective Synthesis of Functionalized Hexahydropyrrolo[3,4-b]pyrroles
T2 - Organic Letters
AU - Rostovskii, Nikolai V
AU - Sakharov, Pavel A
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F
AU - Starova, G. L.
PY - 2015
DA - 2015/08/14
PB - American Chemical Society (ACS)
SP - 4148-4151
IS - 17
VL - 17
PMID - 26271187
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2015_Rostovskii,
author = {Nikolai V Rostovskii and Pavel A Sakharov and Mikhail S. Novikov and Alexander F Khlebnikov and G. L. Starova},
title = {Cu(I)-NHC-Catalyzed (2 + 3)-Annulation of Tetramic Acids with 2H-Azirines: Stereoselective Synthesis of Functionalized Hexahydropyrrolo[3,4-b]pyrroles},
journal = {Organic Letters},
year = {2015},
volume = {17},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.orglett.5b01883},
number = {17},
pages = {4148--4151},
doi = {10.1021/acs.orglett.5b01883}
}
Cite this
MLA
Copy
Rostovskii, Nikolai V., et al. “Cu(I)-NHC-Catalyzed (2 + 3)-Annulation of Tetramic Acids with 2H-Azirines: Stereoselective Synthesis of Functionalized Hexahydropyrrolo[3,4-b]pyrroles.” Organic Letters, vol. 17, no. 17, Aug. 2015, pp. 4148-4151. https://doi.org/10.1021/acs.orglett.5b01883.