Cationic Ir/Me-BIPAM-catalyzed asymmetric intramolecular direct hydroarylation of α-ketoamides

Angew Chem Int Ed Engl. 2014 Mar 3;53(10):2658-61. doi: 10.1002/anie.201400147.

Abstract

Asymmetric intramolecular direct hydroarylation of α-ketoamides gives various types of optically active 3-substituted 3-hydroxy-2-oxindoles in high yields with complete regioselectivity and high enantioselectivities (84-98% ee). This is realized by the use of the cationic iridium complex [Ir(cod)₂](BAr(F)₄) and the chiral O-linked bidentate phosphoramidite (R,R)-Me-BIPAM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Catalysis
  • Cations / chemistry
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Iridium / chemistry*
  • Molecular Structure
  • Organophosphorus Compounds / chemistry*
  • Oxindoles

Substances

  • Amides
  • Cations
  • Indoles
  • Organophosphorus Compounds
  • Oxindoles
  • phosphoramidite
  • 2-oxindole
  • Iridium