Assembly of indoline-2-carboxylate-embodied dipeptides via Pd-catalyzed C(sp2)-H bond direct functionalization

Org Lett. 2015 Feb 6;17(3):496-9. doi: 10.1021/ol503514t. Epub 2015 Jan 20.

Abstract

Intramolecular dehydrogenative cyclization of 2-methoxyiminoacyl-protected phenylalanine derivatives proceeded at 110 °C under catalysis of Pd(OAc)2 in the presence of 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate to afford substituted indoline-2-carboxylates that were converted into indoline-2-carboxylate-embodied dipeptides via Raney Ni-catalyzed hydrogenation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Catalysis
  • Cyclization
  • Dipeptides / chemical synthesis*
  • Dipeptides / chemistry
  • Hydrogenation
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Palladium / chemistry*

Substances

  • Carboxylic Acids
  • Dipeptides
  • Indoles
  • indoline-2-carboxylate
  • Palladium
  • indoline