Control of Azomethine Cycloaddition Stereochemistry by CF3 Group: Structural Diversity of Fluorinated β-Proline Dimers
Konstantin V. Kudryavtsev
1, 2
,
Mikhail N Sokolov
1
,
Stefan Bräse
5, 6
,
Nikolay S. Zefirov
1, 2
,
Publication type: Journal Article
Publication date: 2016-08-30
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
27574905
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.
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Citations from 2024:
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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://pubs.acs.org/doi/10.1021/acs.orglett.6b02327
TI - Control of Azomethine Cycloaddition Stereochemistry by CF3 Group: Structural Diversity of Fluorinated β-Proline Dimers
T2 - Organic Letters
AU - Kudryavtsev, Konstantin V.
AU - Mantsyzov, Alexey B.
AU - Ivantcova, Polina M.
AU - Sokolov, Mikhail N
AU - Churakov, Andrei V.
AU - Bräse, Stefan
AU - Zefirov, Nikolay S.
AU - Polshakov, Vladimir I.
PY - 2016
DA - 2016/08/30
PB - American Chemical Society (ACS)
SP - 4698-4701
IS - 18
VL - 18
PMID - 27574905
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2016_Kudryavtsev,
author = {Konstantin V. Kudryavtsev and Alexey B. Mantsyzov and Polina M. Ivantcova and Mikhail N Sokolov and Andrei V. Churakov and Stefan Bräse and Nikolay S. Zefirov 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://pubs.acs.org/doi/10.1021/acs.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://pubs.acs.org/doi/10.1021/acs.orglett.6b02327.