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

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 08期

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.

引用

页码：1529 / 1532

页数：4

共 59 条

[1] Recent applications of gold catalysis in organic synthesis [J].