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

Organic Letters · 2006 · Vol. 8(8) · pp. 1529–1532

Vanessa Kar‐Yan Lo✉(State Key Laboratory of Synthetic Chemistry)Yungen Liu(University of Hong Kong)Man‐Kin Wong(University of Hong Kong)Chi-Ming Che(State Key Laboratory of Synthetic Chemistry)

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Abstract

[reaction: see text] 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 IC(50) values up to 1.1 microM against a human hepatocellular carcinoma cell line (HepG2) were exhibited by these artemisinin derivatives.

Catalytic Alkyne Reactions Click Chemistry and Applications Catalytic Cross-Coupling ReactionsChemistryCatalysisCoupling reactionArtemisininAmine gas treatingCombinatorial chemistryComponent (thermodynamics)Reaction conditionsCoupling (piping)Organic chemistry

MeSH terms

CatalysisDrug Screening Assays, AntitumorGoldHumansLactonesPargylinePropylaminesSesquiterpenesStereoisomerismMolecular StructureInhibitory Concentration 50ArtemisininsCell Line, Tumor

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365

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15.40

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