Enantioselective intramolecular propargylic amination using chiral copper-pybox complexes as catalysts

Chem Commun (Camb). 2014 Jul 25;50(58):7874-7. doi: 10.1039/c4cc01676a.

Abstract

Intramolecular propargylic amination of propargylic acetates bearing an amino group at the suitable position in the presence of chiral copper-pybox complexes proceeds enantioselectively to give optically active 1-ethynyl-isoindolines (up to 98% ee). The method described in this communication provides a useful synthetic approach to the enantioselective preparation of nitrogen containing heterocyclic compounds with an ethynyl group at the α-position.

MeSH terms

  • Alkynes / chemistry*
  • Amination
  • Catalysis
  • Copper / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Oxazoles / chemistry*
  • Propanols / chemistry*
  • Pyridines / chemistry*
  • Stereoisomerism

Substances

  • (4'S,5'S)-2,6-bis(4'-(triisopropylsilyl)oxymethyl-5'-phenyl-1',3'-oxazolin-2'-yl)pyridine
  • Alkynes
  • Heterocyclic Compounds
  • Oxazoles
  • Propanols
  • Pyridines
  • Copper
  • propargyl alcohol