Chemoselective formation of successive triazole linkages in one pot: " Click-click" chemistry

被引：198

作者：

Aucagne, Vincent ^{[1
]}

Leigh, David A. ^{[1
]}

机构：

[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 20期

关键词：

D O I：

10.1021/ol061657d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A methodology for the successive regiospecific "clicking" together of three components in one pot via two triazole linkages is reported. The protocol utilizes copper(I)-mediated alkyne-azide cycloaddition reactions combined with a silver(I)-catalyzed TMS-alkyne deprotection under mild hydroalcoholic conditions. We exemplify the approach with peptide-based components to illustrate its compatibility with polyfunctionalized biomolecules. The method constitutes a promising tool for peptide ligation. We also provide a procedure for directly using TMS-alkynes as the cycloaddition partner in classical "click" chemistry.

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页码：4505 / 4507

页数：3

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