A mild dihydrobenzooxaphosphole oxazoline/iridium catalytic system for asymmetric hydrogenation of unfunctionalized dialins

Angew Chem Int Ed Engl. 2014 Dec 22;53(52):14428-32. doi: 10.1002/anie.201408929. Epub 2014 Nov 10.

Abstract

Air-stable P-chiral dihydrobenzooxaphosphole oxazoline ligands were designed and synthesized. When they were used in the iridium-catalyzed asymmetric hydrogenation of unfunctionalized 1-aryl-3,4-dihydronaphthalenes under one atmosphere pressure of H2 , up to 99:1 e.r. was obtained. High enantioselectivities were also observed in the reduction of the exocyclic imine derivatives of 1-tetralones.

Keywords: P,N ligands; asymmetric catalysis; imines; iridium; reduction.

MeSH terms

  • Catalysis
  • Hydrogen / chemistry*
  • Hydrogenation
  • Imines / chemistry
  • Iridium / chemistry*
  • Models, Molecular
  • Oxazoles / chemistry*
  • Stereoisomerism

Substances

  • Imines
  • Oxazoles
  • Iridium
  • Hydrogen