Control of Azomethine Cycloaddition Stereochemistry
by CF3 Group: Structural Diversity of Fluorinated β‑Proline
Dimers
Version 2 2016-09-12, 20:27
Version 1 2016-08-30, 19:44
Posted on 2016-08-30 - 00:00
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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Kudryavtsev, Konstantin V.; B. Mantsyzov, Alexey; Ivantcova, Polina
M.; Sokolov, Mikhail N.; Churakov, Andrei V.; Bräse, Stefan; et al. (2016). Control of Azomethine Cycloaddition Stereochemistry
by CF3 Group: Structural Diversity of Fluorinated β‑Proline
Dimers. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.6b02327
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AUTHORS (8)
KK
Konstantin V. Kudryavtsev
AB
Alexey B. Mantsyzov
PI
Polina
M. Ivantcova
MS
Mikhail N. Sokolov
AC
Andrei V. Churakov
SB
Stefan Bräse
NZ
Nikolay
S. Zefirov
VP
Vladimir I. Polshakov
KEYWORDS
aryl groupsProline-functionalizedProlinecycloadditionFluorinatedβ- proline backbone stereogenic centersStructural Diversitymethodologyacrylamide chiral cis conformationelectronegative characterdipolarmethodAzomethine Cycloaddition Stereochemistrydimersstabilizationhomochiral monomeric unitssubstituenttrifluoromethylDimernon-peptidicCF 3 Groupazomethine ylidesreactivity