Highly regioselective synthesis of 2,4,5-(hetero) aryl substituted oxazoles by intermolecular [3+2]-cycloaddition of unsymmetrical internal alkynes

被引：74

作者：

Chatzopoulou, Elli ^{[1
]}

Davies, Paul W. ^{[1
]}

机构：

[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 77期

关键词：

GOLD; CYCLOADDITION; NITRILES; 5-(3-INDOLYL)OXAZOLES; REARRANGEMENT; CATALYSIS; OXIDATION; MOIETIES; YLIDES; ACCESS;

D O I：

10.1039/c3cc45410j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A robust N-nucleophilic 1,3-N,O-dipole equivalent reacts with unsymmetrical internal alkynes under gold catalysis. Conjugation from a remote nitrogen lone pair enables and controls this convergent and highly regioselective process.

引用

页码：8617 / 8619

页数：3

共 41 条

[1] Gold(I)-catalyzed intermolecular addition of carbon nucleophiles to 1,5- and 1,6-enynes [J].

Amijs, Catelijne H. M. ;

Lopez-Carrillo, Veronica ;

Raducan, Mihai ;

Perez-Galan, Patricia ;

Ferrer, Catalina ;

Echavarren, Antonio M. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7721-7730

[2] Regioselective Formation of 2,5-Disubstituted Oxazoles Via Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes [J].

Cano, Israel ;

Alvares, Eleuterio ;

Carmen Nicasio, M. ;

Perez, Pedro J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (02) :191-193

[3] THE PHOTOCHEMISTRY OF ACYL AZIDES .9. DIRECT AND SENSITIZED PHOTOLYTIC GENERATION OF ACYLNITRENES FOR CYCLOADDITION REACTIONS [J].

CLAUSS, KU ;

BUCK, K ;

ABRAHAM, W .

TETRAHEDRON, 1995, 51 (26) :7181-7192

[4]

Dalip K., 2010, EUR J MED CHEM, V45, P1244

[5] Control of competing N-H insertion and Wolff rearrangement in dirhodium(II)-catalyzed reactions of 3-indolyl diazoketoesters. Synthesis of a potential precursor to the marine 5-(3-indolyl)oxazole martefragin A [J].

Davies, JR ;

Kane, PD ;

Moody, CJ ;

Slawin, AMZ .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (15) :5840-5851

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

Davies, Paul W. ;

Cremonesi, Alex ;

Dumitrescu, Lidia .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) :8931-8935

[7] Site-specific introduction of gold-carbenoids by intermolecular oxidation of ynamides or ynol ethers [J].

Davies, Paul W. ;

Cremonesi, Alex ;

Martin, Nicolas .

CHEMICAL COMMUNICATIONS, 2011, 47 (01) :379-381

[8] Nitrene Chemistry in Organic Synthesis: Still in Its Infancy? [J].

Dequirez, Geoffroy ;

Pons, Valerie ;

Dauban, Philippe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (30) :7384-7395

[9] Catalytic carbophilic activation:: Catalysis by platinum and gold π acids [J].

Fuerstner, Alois ;

Davies, Paul W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) :3410-3449

[10] Hyperbranched poly(aryl ether oxazole)s: Synthesis, characterization, and modification [J].

Gong, ZH ;

Leu, CM ;

Wu, FI ;

Shu, CF .

MACROMOLECULES, 2000, 33 (23) :8527-8533

← 1 2 3 4 5 →