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

J Org Chem. 2021 Sep 3;86(17):12054-12063. doi: 10.1021/acs.joc.1c01415. Epub 2021 Aug 10.

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).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hydrogenation
  • Kinetics
  • Ruthenium*
  • Stereoisomerism

Substances

  • Ruthenium