Iridium Catalysts with f-Amphox Ligands: Asymmetric Hydrogenation of Simple Ketones

Org Lett. 2016 Jun 17;18(12):2938-41. doi: 10.1021/acs.orglett.6b01290. Epub 2016 Jun 3.

Abstract

A series of modular and rich electronic tridentate ferrocene aminophosphoxazoline ligands (f-amphox) have been successfully developed and used in iridium-catalytic asymmetric hydrogenation of simple ketones to afford corresponding enantiomerically enriched alcohols under mild conditions with superb activities and excellent enantioselectivities (up to 1 000 000 TON, almost all products up to >99% ee, full conversion). The resulting chiral alcohols and their derivatives are important intermediates in pharmaceuticals.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Catalysis
  • Ferrous Compounds / chemical synthesis*
  • Ferrous Compounds / chemistry
  • Hydrogenation
  • Iridium / chemistry*
  • Ketones / chemistry*
  • Ligands
  • Metallocenes / chemical synthesis*
  • Metallocenes / chemistry
  • Models, Molecular
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry
  • Stereoisomerism
  • Thermodynamics

Substances

  • Alcohols
  • Ferrous Compounds
  • Ketones
  • Ligands
  • Metallocenes
  • Oxazoles
  • Iridium
  • ferrocene