title: Control of Azomethine Cycloaddition Stereochemistry by CF3 Group: Structural Diversity of Fluorinated β-Proline Dimers.
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.
authors: Department of Chemistry, Lomonosov Moscow State University , Leninskie Gory 1/3, Moscow 119991, Russian Federation.|Institute of Physiologically Active Compounds, Russian Academy of Sciences , Chernogolovka, Moscow Region 142432, Russian Federation.
authors: Konstantin V
authors: KV
authors: Kudryavtsev
authors: Faculty of Fundamental Medicine, Lomonosov Moscow State University , Lomonosovsky Ave 31/5, Moscow 119992, Russian Federation.
authors: Alexey B
authors: AB
authors: Mantsyzov
authors: Department of Chemistry, Lomonosov Moscow State University , Leninskie Gory 1/3, Moscow 119991, Russian Federation.
authors: Polina M
authors: PM
authors: Ivantcova
authors: Department of Chemistry, Lomonosov Moscow State University , Leninskie Gory 1/3, Moscow 119991, Russian Federation.
authors: Mikhail N
authors: MN
authors: Sokolov
authors: Institute of General and Inorganic Chemistry, Russian Academy of Sciences , Leninskii prosp. 31, Moscow 119991, Russian Federation.
authors: Andrei V
authors: AV
authors: Churakov
authors: Institute of Organic Chemistry, Karlsruhe Institute of Technology , Fritz-Haber-Weg 6, Karlsruhe 76131, Germany.|Institute of Toxicology and Genetics, Karlsruhe Institute of Technology , Hermann-von-Helmholtz-Platz 1, Eggenstein-Leopoldshafen 76344, Germany.
authors: Stefan
authors: S
authors: Bräse
authors: Department of Chemistry, Lomonosov Moscow State University , Leninskie Gory 1/3, Moscow 119991, Russian Federation.|Institute of Physiologically Active Compounds, Russian Academy of Sciences , Chernogolovka, Moscow Region 142432, Russian Federation.
authors: Nikolay S
authors: NS
authors: Zefirov
authors: Faculty of Fundamental Medicine, Lomonosov Moscow State University , Lomonosovsky Ave 31/5, Moscow 119992, Russian Federation.|NMR Laboratory, Institute of Physics, Kazan Federal University , Kremlevskaya 18, Kazan 420008, Russian Federation.
authors: Vladimir I
authors: VI
authors: Polshakov