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

被引:355
作者
Lo, VKY
Liu, YG
Wong, MK
Che, CM
机构
[1] Univ Hong Kong, Inst Mol Technol Drug Discovery & Synth, Dept Chem, Hong Kong, Hong Kong, Peoples R China
[2] Univ Hong Kong, Inst Mol Technol Drug Discovery & Synth, Open Lab Chem Biol, Hong Kong, Hong Kong, Peoples R China
关键词
D O I
10.1021/ol0528641
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
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收藏
页码:1529 / 1532
页数:4
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