Asymmetric Transfer Hydrogenation of gem ‐Difluorocyclopropenyl Esters: Access to Enantioenriched gem ‐Difluorocyclopropanes
| Autor: | Khalil Yamani, Christophe Meyer, Alexis Archambeau, Hugo Pierre, Janine Cossy |
|---|---|
| Přispěvatelé: | Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL), Chimie Moléculaire, Macromoléculaire et Matériaux (UMR7167) (C3M), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC) |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Hydrogen
010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Chiral ligand Enantioselective synthesis chemistry.chemical_element Homogeneous catalysis General Chemistry General Medicine 010402 general chemistry Transfer hydrogenation 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry [CHIM]Chemical Sciences ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Angewandte Chemie International Edition Angewandte Chemie International Edition, Wiley-VCH Verlag, 2020, 59 (42), pp.18505-18509. ⟨10.1002/anie.202008572⟩ |
| ISSN: | 1433-7851 1521-3773 |
| Popis: | Catalytic enantioselective access to disubstituted functionalized gem-difluorocyclopropanes, which are emerging fluorinated motifs of interest in medicinal chemistry, was achieved through asymmetric transfer hydrogenation of gem-difluorocyclopropenyl esters, catalyzed by a Noyori-Ikariya (p-cymene)-ruthenium(II) complex, with (N-tosyl-1,2-diphenylethylenediamine) as the chiral ligand and isopropanol as the hydrogen donor. The resulting cis-gem-difluorocyclopropyl esters were obtained with moderate to high enantioselectivity (ee=66-99 %), and post-functionalization reactions enable access to valuable building blocks incorporating a cis- or trans-gem-difluorocyclopropyl motif. |
| Databáze: | OpenAIRE |
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