Gold(III) salen complex-catalyzed synthesis of propargylamines via a three-component coupling reaction

Propargylamines have been synthesized by a gold(III) salen complex-catalyzed three-component coupling reaction of aldehydes, amines, and alkynes in water in excellent yields at 40 degrees C. With chiral prolinol derivatives as the amine component, excellent diastereoselectivities (up to 99:1) have been attained. This coupling reaction has been applied to the synthesis of propargylamine-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. Cytotoxicities with IC50 values up to 1.1 mu M against a human hepatocellular carcinoma cell line (HepG2) were exhibited by these artemisinin derivatives.