Organic Letters, volume 18, issue 18, pages 4698-4701
Control of Azomethine Cycloaddition Stereochemistry by CF3 Group: Structural Diversity of Fluorinated β-Proline Dimers
Kudryavtsev Konstantin V.
1, 2
,
Sokolov Mikhail N
1
,
Bräse Stefan
5, 6
,
Zefirov Nikolay S.
1, 2
,
Publication type: Journal Article
Publication date: 2016-08-30
Journal:
Organic Letters
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.2
ISSN: 15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
β-Proline-functionalized dimers consisting of homochiral monomeric units were synthesized by a non-peptidic coupling method for the first time. The applied synthetic methodology is based on 1,3-dipolar cycloaddition chemistry of azomethine ylides and provides absolute control over the β-proline backbone stereogenic centers. An o-(trifluoromethyl)phenyl substituent contributes to appropriate stabilization of the definite acrylamide chiral cis conformation and to achieve the dipole reactivity that is not observed for aryl groups lacking strong electronegative character.
Citations by journals
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1
2
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Journal of Organic Chemistry
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Journal of Organic Chemistry
2 publications, 25%
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Acta Crystallographica Section E: Crystallographic Communications
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Acta Crystallographica Section E: Crystallographic Communications
1 publication, 12.5%
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Beilstein Journal of Organic Chemistry
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Beilstein Journal of Organic Chemistry
1 publication, 12.5%
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Molecules
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Molecules
1 publication, 12.5%
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Chirality
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Chirality
1 publication, 12.5%
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ChemistrySelect
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ChemistrySelect
1 publication, 12.5%
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Synthesis
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Synthesis
1 publication, 12.5%
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1
2
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Citations by publishers
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1
2
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|
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American Chemical Society (ACS)
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American Chemical Society (ACS)
2 publications, 25%
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Wiley
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Wiley
2 publications, 25%
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International Union of Crystallography (IUCr)
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International Union of Crystallography (IUCr)
1 publication, 12.5%
|
|
Beilstein-Institut
|
Beilstein-Institut
1 publication, 12.5%
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 12.5%
|
|
Thieme
|
Thieme
1 publication, 12.5%
|
|
1
2
|
- 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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Kudryavtsev K. V. et al. Control of Azomethine Cycloaddition Stereochemistry by CF3 Group: Structural Diversity of Fluorinated β-Proline Dimers // Organic Letters. 2016. Vol. 18. No. 18. pp. 4698-4701.
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Kudryavtsev K. V., Mantsyzov A. B., Ivantcova P. M., Sokolov M. N., Churakov A. V., Bräse S., Zefirov N. S., Polshakov V. I. Control of Azomethine Cycloaddition Stereochemistry by CF3 Group: Structural Diversity of Fluorinated β-Proline Dimers // Organic Letters. 2016. Vol. 18. No. 18. pp. 4698-4701.
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TY - JOUR
DO - 10.1021/acs.orglett.6b02327
UR - https://doi.org/10.1021%2Facs.orglett.6b02327
TI - Control of Azomethine Cycloaddition Stereochemistry by CF3 Group: Structural Diversity of Fluorinated β-Proline Dimers
T2 - Organic Letters
AU - Zefirov, Nikolay S.
AU - Kudryavtsev, Konstantin V.
AU - Mantsyzov, Alexey B.
AU - Ivantcova, Polina M.
AU - Sokolov, Mikhail N
AU - Churakov, Andrei V.
AU - Bräse, Stefan
AU - Polshakov, Vladimir I.
PY - 2016
DA - 2016/08/30 00:00:00
PB - American Chemical Society (ACS)
SP - 4698-4701
IS - 18
VL - 18
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2016_Kudryavtsev,
author = {Nikolay S. Zefirov and Konstantin V. Kudryavtsev and Alexey B. Mantsyzov and Polina M. Ivantcova and Mikhail N Sokolov and Andrei V. Churakov and Stefan Bräse and Vladimir I. Polshakov},
title = {Control of Azomethine Cycloaddition Stereochemistry by CF3 Group: Structural Diversity of Fluorinated β-Proline Dimers},
journal = {Organic Letters},
year = {2016},
volume = {18},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021%2Facs.orglett.6b02327},
number = {18},
pages = {4698--4701},
doi = {10.1021/acs.orglett.6b02327}
}
Cite this
MLA
Copy
Kudryavtsev, Konstantin V., et al. “Control of Azomethine Cycloaddition Stereochemistry by CF3 Group: Structural Diversity of Fluorinated β-Proline Dimers.” Organic Letters, vol. 18, no. 18, Aug. 2016, pp. 4698-4701. https://doi.org/10.1021%2Facs.orglett.6b02327.