Chiral FLP-catalyzed asymmetric hydrogenation of 3-fluorinated chromones

Chem Commun (Camb). 2022 Feb 1;58(10):1558-1560. doi: 10.1039/d1cc06964k.

Abstract

The asymmetric hydrogenation of fluorinated olefins is an efficient pathway towards the synthesis of chiral fluorine-containing compounds. This paper described metal-free asymmetric hydrogenation of 3-fluorinated chromones with the use of readily available achiral borane and chiral oxazoline as an FLP catalyst for the first time. A variety of optically active 3-fluorochroman-4-ones were obtained in high yields with up to 88% ee.

MeSH terms

  • Boranes / chemistry
  • Catalysis
  • Chromones / chemistry*
  • Fluorine / chemistry
  • Hydrogenation
  • Lewis Acids / chemistry*
  • Oxazoles / chemistry
  • Stereoisomerism

Substances

  • Boranes
  • Chromones
  • Lewis Acids
  • Oxazoles
  • Fluorine