Gold(III) Salen Complex-Catalyzed Synthesis of Propargylamines via a Three-Component Coupling Reaction

Vanessa Kar-Yan Lo, Yungen Liu, Man-Kin Wong,* and Chi-Ming Che*;
Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, China
Org. Lett., 2006, 8 (8), pp 1529–1532
DOI: 10.1021/ol0528641
Publication Date (Web): March 17, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, cmche@hku.hk, ; , mkwong@hkusua.hku.hk

Abstract

Abstract Image

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 °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 μM against a human hepatocellular carcinoma cell line (HepG2) were exhibited by these artemisinin derivatives.

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History

  • Published In Issue April 13, 2006
  • Received November 25, 2005

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