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

Abstract

The one-pot three-component reaction of terminal alkynes, aldehydes and secondary amines in the presence of copper(1) 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. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.