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
相关论文
共 96 条
  • [91] Alkynes as Equivalents of α-Diazo Ketones in Generating α-Oxo Metal Carbenes: A Gold-Catalyzed Expedient Synthesis of Dihydrofuran-3-ones
    Ye, Longwu
    Cui, Li
    Zhang, Guozhu
    Zhang, Liming
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) : 3258 - +
  • [92] Yeom H.-S., 2010, Angew. Chem, V122, P1655
  • [93] Gold-catalyzed waste-free generation and reaction of azomethine ylides: Internal redox/dipolar cycloaddition cascade
    Yeom, Hyttn-Suk
    Lee, Ji-Eun
    Shin, Setinghoon
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (37) : 7040 - 7043
  • [94] Stereoselective One-Pot Synthesis of 1-Aminoindanes and 5,6 Fused Azacycles Using a Gold-Catalyzed Redox-Pinacol-Mannich-Michael Cascade
    Yeom, Hyun-Suk
    Lee, Youngun
    Jeong, Jaewon
    So, Eunsoo
    Hwang, Soojin
    Lee, Ji-Eun
    Lee, Shim Sung
    Shin, Seunghoon
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (09) : 1611 - 1614
  • [95] Geometry-dependent divergence in the gold-catalyzed redox cascade cyclization of o-alkynylaryl ketoximes and nitrones leading to isoindoles
    Yeom, Hyun-Suk
    Lee, Youngun
    Lee, Ji-Eun
    Shin, Seunghoon
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (22) : 4744 - 4752
  • [96] Tandem azidination- and hydroazidination-Huisgen [3+2] cycloadditions of ynamides. Synthesis of chiral amide-substituted triazoles
    Zhang, Xuejun
    Hsung, Richard P.
    You, Lingfeng
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (14) : 2679 - 2682
12345678910