4,5-Dihydropyrrolo[1,2-a]quinoxalines: a tunable and regenerable biomimetic hydrogen source

Org Lett. 2014 Mar 7;16(5):1406-9. doi: 10.1021/ol500176v. Epub 2014 Feb 26.

Abstract

A series of tunable and regenerable biomimetic hydrogen sources, 4,5-dihydropyrrolo[1,2-a]quinoxalines, have been synthesized and applied in biomimetic asymmetric hydrogenation of 3-aryl-2H-benzo[b][1,4]oxazines and 1-alkyl-3-aryl-quinoxalin-2(1H)-ones, providing the chiral amines with up to 92% and 89% ee, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Benzoxazines / chemical synthesis*
  • Benzoxazines / chemistry
  • Biomimetics
  • Catalysis
  • Hydrogen / chemistry
  • Hydrogenation
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Quinoxalines / chemistry*

Substances

  • Amines
  • Benzoxazines
  • Pyrroles
  • Quinoxalines
  • Hydrogen