Asymmetric Transfer Hydrogenation of gem-Difluorocyclopropenyl Esters: Access to Enantioenriched gem-Difluorocyclopropanes |
| |
Authors: | Khalil Yamani Hugo Pierre Dr Alexis Archambeau Dr Christophe Meyer Prof?Dr Janine Cossy |
| |
Institution: | Molecular, Macromolecular Chemistry, and Materials, ESPCI Paris, PSL University, CNRS, 10 rue Vauquelin, 75005 Paris, France |
| |
Abstract: | 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. |
| |
Keywords: | asymmetric catalysis difluorocyclopropanes difluorocyclopropenes homogeneous catalysis transfer hydrogenation |
|
|