- Journal
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Année
- 2020
- Volume
- 59
- Numéro
- 42
- Pages
- 18505-18509
- Mois
- OCT 12
- DOI
- 10.1002/anie.202008572
Abstract
Catalytic enantioselective access to disubstituted functionalizedgem-difluorocyclopropanes, which are emerging fluorinated motifs of interest in medicinal chemistry, was achieved through asymmetric transfer hydrogenation ofgem-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 resultingcis-gem-difluorocyclopropyl esters were obtained with moderate to high enantioselectivity (ee=66-99 %), and post-functionalization reactions enable access to valuable building blocks incorporating acis- ortrans-gem-difluorocyclopropyl motif.