Highly efficient and versatile synthesis of lactams and N-heterocycles via Al(OTf)3-catalyzed cascade cyclization and ionic hydrogenation reactions

Org Lett. 2014 Jan 3;16(1):190-2. doi: 10.1021/ol403173x. Epub 2013 Dec 6.

Abstract

The discovery and development of an efficient and versatile method for the synthesis of N-substituted lactams is described. Pyrrolindinones, piperidones, and structurally related heterocycles were formed by Al(OTf)3-catalyzed cascade cyclization and ionic hydrogenation reactions of corresponding nitrogen substituted ketoamides in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Hydrogenation
  • Ions / chemistry
  • Lactams / chemical synthesis*
  • Lactams / chemistry
  • Mesylates / chemistry*
  • Molecular Structure

Substances

  • Heterocyclic Compounds
  • Ions
  • Lactams
  • Mesylates
  • trifluoromethanesulfonic acid