ol6b02327_si_001.pdf (3.81 MB)
Control of Azomethine Cycloaddition Stereochemistry by CF3 Group: Structural Diversity of Fluorinated β‑Proline Dimers
journal contribution
posted on 2016-08-30, 19:44 authored by Konstantin V. Kudryavtsev, Alexey B. Mantsyzov, Polina
M. Ivantcova, Mikhail N. Sokolov, Andrei V. Churakov, Stefan Bräse, Nikolay
S. Zefirov, Vladimir I. Polshakovβ-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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aryl groupsProline-functionalizedProlinecycloadditionFluorinatedβ- proline backbone stereogenic centersStructural Diversitymethodologyacrylamide chiral cis conformationelectronegative characterdipolarmethodAzomethine Cycloaddition Stereochemistrydimersstabilizationhomochiral monomeric unitssubstituenttrifluoromethylDimernon-peptidicCF 3 Groupazomethine ylidesreactivity
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