Practical highly enantioselective synthesis of propargylamines through a copper-catalyzed one-pot three-component condensation reaction

Chemistry. 2006 May 24;12(16):4380-92. doi: 10.1002/chem.200501233.

Abstract

The one-pot three-component reaction of terminal alkynes, aldehydes and secondary amines in the presence of copper(I) bromide/quinap is reported. The reaction scope has been determined and a broad variety of all three components has been used, which afforded the corresponding propargylamines in good to excellent yields and moderate to very good enantioselectivities. The reaction showed a strong positive nonlinear effect. The transformation of a propargylamine intermediate into the alkaloid (S)-(+)-coniine has also been described.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Alkynes / chemistry
  • Amines / chemistry
  • Bromides / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Pargyline / analogs & derivatives*
  • Pargyline / chemical synthesis
  • Propylamines / chemical synthesis*
  • Stereoisomerism

Substances

  • Aldehydes
  • Alkynes
  • Amines
  • Bromides
  • Propylamines
  • cupric bromide
  • propargylamine
  • Copper
  • Pargyline