Ru(II)-Catalyzed Asymmetric Transfer Hydrogenation of 3-Fluorochromanone Derivatives to Access Enantioenriched cis-3-Fluorochroman-4-ols through Dynamic Kinetic Resolution.

Abstract

Enantioenriched cis-3-fluoro-chroman-4-ol derivatives were conveniently prepared by the ruthenium-catalyzed asymmetric transfer hydrogenation of a new family of 3-fluoro-chromanones through a dynamic kinetic resolution process. The reaction proceeded under mild conditions using a low catalyst loading and HCO2H/Et3N (1:1) as the hydrogen source, affording the reduced fluorinated alcohols in good yields (80-96%), high diastereomeric ratios (up to 99:1 dr), and excellent enantioselectivities (up to >99% ee).