Cu(I)-NHC-Catalyzed (2 + 3)-Annulation of Tetramic Acids with 2H-Azirines: Stereoselective Synthesis of Functionalized Hexahydropyrrolo[3,4-b]pyrroles

Org Lett. 2015 Sep 4;17(17):4148-51. doi: 10.1021/acs.orglett.5b01883. Epub 2015 Aug 14.

Abstract

A stereoselective and high-yield synthesis of hexahydropyrrolo[3,4-b]pyrroles from tetramic acids and 2H-azirines under Cu(I)-NHC catalysis is developed. An unusual N-C2 azirine bond cleavage, initiated by a copper enolate, was rationalized in terms of a free radical reaction mechanism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azirines / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Iodides / chemistry*
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Pyrrolidinones / chemistry*
  • Stereoisomerism

Substances

  • Azirines
  • Iodides
  • Pyrroles
  • Pyrrolidinones
  • tetramic acid
  • Copper
  • cuprous iodide