Intermolecular and Selective Synthesis of 2,4,5-Trisubstituted Oxazoles by a Gold-Catalyzed Formal [3+2] Cycloaddition

被引：209
|
作者：
Davies, Paul W. [1 ]
Cremonesi, Alex [1 ]
Dumitrescu, Lidia [1 ]
机构：
[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 38期
关键词：
1,3-oxazoles; cycloaddition; gold; homogeneous catalysis; ynamides; ONE-POT SYNTHESIS; PROPARGYLIC ALCOHOLS; SUBSTITUTED OXAZOLES; EFFICIENT SYNTHESIS; CYCLIZATION; ALKYNE; COPPER; YNAMIDES; YLIDES; PHOTOCHEMISTRY;
D O I：
10.1002/anie.201103563
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Oxazole new world: A gold-catalyzed intermolecular reaction of pyridine-N-aminides with ynamides can be used to prepare trisubstituted 1,3-oxazoles with a variety of functional groups. This formal [3+2] cycloaddition employs robust conjugated N-ylides as N-nucleophilic N-acyl nitrene equivalents for a highly chemoselective and regioselective addition across electron-rich C-C triple bonds. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：8931 / 8935
页数：5
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