Dehydrogenative cross-coupling reaction by cooperative transition-metal and Brønsted acid catalysis for the synthesis of β-quinolinyl α-amino acid esters

Org Lett. 2014 Sep 19;16(18):4881-3. doi: 10.1021/ol502402s. Epub 2014 Sep 9.

Abstract

A novel dehydrogenative cross-coupling (DCC) reaction between methylquinoline derivatives and N-aryl glycine esters was developed by a cooperative catalysis of copper salt and Brønsted acid, affording an efficient synthesis of β-quinolinyl α-amino acid esters. A plausible mechanism using a proton to activate the methylquinoline derivative and copper(II) to activate N-aryl glycine ester has been proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Catalysis
  • Copper / chemistry
  • Esters
  • Glycine / chemistry
  • Glycine / metabolism
  • Molecular Structure
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Stereoisomerism
  • Transition Elements

Substances

  • Amino Acids
  • Esters
  • Quinolines
  • Transition Elements
  • Copper
  • Glycine