Iridium-catalyzed asymmetric hydrogenation of pyrrolo[1,2-a]pyrazinium salts

Org Lett. 2014 Jun 20;16(12):3324-7. doi: 10.1021/ol5013313. Epub 2014 Jun 9.

Abstract

Highly enantioselective iridium-catalyzed hydrogenation of pyrrolo[1,2-a]pyrazinium salts has been achieved, providing a direct access to chiral 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine derivatives with up to 95% ee. The key feature of the reaction is the addition of cesium carbonate, which increases the conversion and prohibits the racemization pathway of products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbonates / chemistry
  • Catalysis
  • Cesium / chemistry
  • Hydrogenation
  • Iridium / chemistry*
  • Molecular Structure
  • Pyrazines / chemical synthesis
  • Pyrazines / chemistry*
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry*
  • Salts

Substances

  • Carbonates
  • Pyrazines
  • Pyrroles
  • Salts
  • Cesium
  • Iridium
  • cesium carbonate