Straightforward Access to Enantioenriched <i>cis</i>-3-Fluoro-dihydroquinolin-4-ols Derivatives via Ru(II)-Catalyzed-Asymmetric Transfer Hydrogenation/Dynamic Kinetic Resolution
Ricardo Molina Betancourt,
Phannarath Phansavath,
Virginie Ratovelomanana-Vidal
Affiliations
Ricardo Molina Betancourt
CSB2D Team, CNRS, UMR 8060, Chimie ParisTech, Institute of Chemistry for Life and Health Sciences, PSL University, 75005 Paris, France
Phannarath Phansavath
CSB2D Team, CNRS, UMR 8060, Chimie ParisTech, Institute of Chemistry for Life and Health Sciences, PSL University, 75005 Paris, France
Virginie Ratovelomanana-Vidal
CSB2D Team, CNRS, UMR 8060, Chimie ParisTech, Institute of Chemistry for Life and Health Sciences, PSL University, 75005 Paris, France
Herein we report a practical method for the asymmetric transfer hydrogenation/dynamic kinetic resolution of N-Boc 3-fluoro-dihydrotetrahydroquinolin-4-ones into the corresponding cis-fluoro alcohols in 70–96% yields, up to 99:1 diastereomeric ratio (dr) and up to >99% ee (enantiomeric excess) by using the ruthenium complex Ts-DENEB and a formic acid/triethylamine (1:1) mixture as the hydrogen donor under mild conditions.
