Rapid Access to Chroman-3-ones through Gold-Catalyzed Oxidation of Propargyl Aryl Ethers

被引：132

作者：

Wang, Yanzhao ^{[1
]}

Ji, Kegong ^{[1
]}

Lan, Sylvester ^{[1
]}

Zhang, Liming ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 08期

关键词：

carbenes; gold; heterocycles; homogeneous catalysis; oxidation; ALPHA-DIAZO KETONES; EFFICIENT SYNTHESIS; PHOSPHINE; 1,5-ENYNES; COMPLEXES; ALKYNES;

D O I：

10.1002/anie.201107561

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The two-step: Chroman-3-ones are important intermediates for organic synthesis and medicinal chemistry. However, their syntheses require multiple steps and are not efficient. By using gold-catalyzed alkyne oxidation, this versatile heterocycle can be prepared in only two steps from readily available phenols and with mostly high efficiencies (see scheme). © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1915 / 1918

页数：4

共 47 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]

[Anonymous], 2011, ANGEW CHE

[3] Synthesis of Fused Carbocycles via a Selective 6-Endo Dig Gold(I)-Catalyzed Carbocyclization [J].

Barabe, Francis ;

Levesque, Patrick ;

Korobkov, Ilia ;

Barriault, Louis .

ORGANIC LETTERS, 2011, 13 (20) :5580-5583

[4]

Burgos C. H., 2006, ANGEW CHEM, V118, P4427

[5] Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects [J].

Burgos, Carlos H. ;

Barder, Timothy E. ;

Huang, Xiaohua ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4321-4326

[6] Percent buried volume for phosphine and N-heterocyclic carbene ligands: steric properties in organometallic chemistry [J].

Clavier, Herve ;

Nolan, Steven P. .

CHEMICAL COMMUNICATIONS, 2010, 46 (06) :841-861

[7] ENANTIOSELECTIVE TOTAL SYNTHESIS OF MIROESTROL [J].

COREY, EJ ;

WU, LI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (20) :9327-9328

[8]

DANAN A, 1991, B SOC CHIM FR, P189

[9] 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

[10]

Dorwald F.Z., 1999, METAL CARBENES ORGAN

← 1 2 3 4 5 →