Bio- and Medicinally Compatible α-Amino-Acid Modification via Merging Photoredox and N-Heterocyclic Carbene Catalysis

Org Lett. 2020 Aug 21;22(16):6370-6375. doi: 10.1021/acs.orglett.0c02202. Epub 2020 Aug 5.

Abstract

An N-heterocyclic carbene and photoredox cocatalyzed α-amino-acid decarboxylative carbonylation reaction is presented. This method displays good scope generality, providing a direct pathway to access various downstream α-amino ketones under bio- and medicinally compatible conditions. Moreover, this strategy is appealing to chemical biology because it has great potential for the chemical modification of peptides or the late-stage synthesis of keto-peptides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Amino Acids / metabolism
  • Catalysis
  • Heterocyclic Compounds / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Amino Acids
  • Heterocyclic Compounds
  • Ketones
  • carbene
  • Methane