Gold(III) salen complex-catalyzed synthesis of propargylamines via a three-component coupling reaction
Gold(III) salen complex-catalyzed synthesis of propargylamines via a three-component coupling reaction
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DOI：
10.1021/ol0528641
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发表时间：
2006-04-13
期刊：
影响因子：
5.2
通讯作者：
Che, CM
中科院分区：
文献类型：
--
作者：
Lo, VKY;Liu, YG;Che, CM
用金（III） salen络合物催化醛、胺和炔在水中的三组分偶联反应，在40℃下以优异的产率合成了丙炔胺。以手性脯氨酸醇衍生物为胺组分，获得了优异的非对映选择性（高达99:1）。该偶联反应已被用于合成丙胺修饰的青蒿素衍生物，其精致的内过氧化物部分保持完整。这些青蒿素衍生物对人肝癌细胞系（HepG2）的IC50值高达1.1 μ M。
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.