Control of Azomethine Cycloaddition Stereochemistry by CF3 Group: Structural Diversity of Fluorinated β-Proline Dimers
| Autor: | Vladimir I. Polshakov, Stefan Bräse, Andrei V. Churakov, Alexey B. Mantsyzov, Mikhail N. Sokolov, Konstantin V. Kudryavtsev, Nikolay S. Zefirov, Polina M. Ivantcova |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Trifluoromethyl
010405 organic chemistry Stereochemistry Aryl Organic Chemistry Substituent 010402 general chemistry 01 natural sciences Biochemistry Cycloaddition 0104 chemical sciences Stereocenter chemistry.chemical_compound Monomer chemistry Acrylamide Reactivity (chemistry) Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 18:4698-4701 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.6b02327 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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