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 °C. With chiral prolinol derivatives as the amine component, excellent diastereoselectivities (up to 99:1) have been att...

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Veröffentlicht in:	Organic letters 2006-04, Vol.8 (8), p.1529-1532
Hauptverfasser:	Lo, Vanessa Kar-Yan, Liu, Yungen, Wong, Man-Kin, Che, Chi-Ming
Format:	Artikel
Sprache:	eng
Schlagworte:	Artemisinins - chemical synthesis Artemisinins - chemistry Artemisinins - pharmacology Catalysis Cell Line, Tumor Drug Screening Assays, Antitumor Gold - chemistry Humans Inhibitory Concentration 50 Lactones - chemical synthesis Lactones - chemistry Lactones - pharmacology Molecular Structure Pargyline - analogs & derivatives Pargyline - chemical synthesis Pargyline - chemistry Propylamines - chemical synthesis Propylamines - chemistry Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Sesquiterpenes - pharmacology Stereoisomerism
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Zusammenfassung:	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.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol0528641