RESUMO
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.
RESUMO
Straightforward access to enantiomerically enriched cis-3-benzyl-chromanols from (E)-3-benzylidene-chromanones was developed through Rh-catalyzed asymmetric transfer hydrogenation. This transformation allowed the reduction of both the CâC and CâO bonds and the formation of two stereocenters in high yields with excellent levels of diastereo- and enantioselectivities (up to >99:1 dr, up to >99% ee) in a single step through a dynamic kinetic resolution process using a low catalyst loading and HCO2H/DABCO as the hydrogen source.