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

收藏

页码：1529 / 1532

页数：4

相关论文

共 59 条

[31] Ruthenium(II) porphyrin catalyzed imine aziridination and crystal structures of (meso-tetrakis(pentafluorophenyl)porphyrinato)ruthenium(II) complexes containing PhN=CH(p-ClPh), CPh2, and pyridine ligands [J].

Li, Y ;

Chan, PWH ;

Zhu, NY ;

Che, CM ;

Kwong, HL .

ORGANOMETALLICS, 2004, 23 (01) :54-66

[32] Synthesis and cytotoxicity studies of artemisinin derivatives containing lipophilic alkyl carbon chains [J].

Liu, YG ;

Wong, VKW ;

Ko, BCB ;

Wong, MK ;

Che, CM .

ORGANIC LETTERS, 2005, 7 (08) :1561-1564

[33] Catalaytic isomerization of 1,5-enynes to bicyclo [3.1.0]hexenes [J].

Luzung, MR ;

Markham, JP ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (35) :10858-10859

[34] Syntheses and antimalarial activities of 10-substituted deoxoartemisinins [J].

Ma, JY ;

Katz, E ;

Kyle, DE ;

Ziffer, H .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (22) :4228-4232

[35] Gold(I)-catalyzed ring expansion of cyclopropanols and cyclobutanols [J].

Markham, JP ;

Staben, ST ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (27) :9708-9709

[36] Phosphine gold(I) Bis-(trifluoromethanesulfonyl)imidate complexes as new highly efficient and air-stable catalysts for the cycloisomerization of enynes [J].

Mézailles, N ;

Ricard, L ;

Gagosz, F .

ORGANIC LETTERS, 2005, 7 (19) :4133-4136

[37] Synthesis of tertiary propargylamines by sequential reactions of in situ generated thioiminium salts with organolithium and -magnesium reagents [J].

Murai, T ;

Mutoh, Y ;

Ohta, Y ;

Murakami, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :5968-5969

[38] Intramolecular [4+2] cycloadditions of 1,3-enynes or arylalkynes with alkenes with highly reactive cationic phosphine Au(I) complexes [J].

Nieto-Oberhuber, C ;

López, S ;

Echavarren, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6178-6179

[39] A medicinal chemistry perspective on artemisinin and related endoperoxides [J].

O'Neill, PM ;

Posner, GH .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (12) :2945-2964

[40] SYNTHESIS AND ANTICHOLINERGIC ACTIVITY OF ESTER AND AMIDE DERIVATIVES OF 2-SUBSTITUTED PIPERIDINES [J].

RYAN, CW ;

AINSWORTH, C .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (05) :1547-&

← 1 2 3 4 5 6 →