[Ir(P-OP)]-catalyzed asymmetric hydrogenation of diversely substituted C═N-containing heterocycles

Org Lett. 2013 Apr 19;15(8):2066-9. doi: 10.1021/ol400854a. Epub 2013 Apr 10.

Abstract

Iridium(I) complexes of enantiomerically pure phosphine-phosphite ligands ([Ir(Cl)(cod)(P-OP)]) efficiently catalyze the enantioselective hydrogenation of diverse C═N-containing heterocyclic compounds (benzoxazines, benzoxazinones, benzothiazinones, and quinoxalinones; 25 examples, up to 99% ee). A substrate-to-catalyst ratio as high as 2000:1 was reached.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Heterocyclic Compounds, 2-Ring / chemical synthesis*
  • Heterocyclic Compounds, 2-Ring / chemistry*
  • Hydrogenation
  • Iridium / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Heterocyclic Compounds, 2-Ring
  • Iridium