On the nature of the reactive intermediates in gold-catalyzed cycloisomerization reactions

被引：229

作者：

Fuerstner, Alois ^{[1
]}

Morency, Louis ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 27期

关键词：

carbenes; carbocations; gold; homogeneous catalysis; platinum;

D O I：

10.1002/anie.200800934

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented). A gold rush: The Stork-Eschenmoser postulate explaining the course and stereoselectivity of cationic polyene cyclization reactions also holds true for cycloisomerization reactions catalyzed by gold. This result suggests that the pertinent intermediates (see scheme) are more adequately described as gold-stabilized carbocations rather than as gold carbenes. E = COOMe, L = neutral ligand. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5030 / 5033

页数：4

共 46 条

[1] Gold(I)-catalysed arylation of 1,6-enynes: different site reactivity of cyclopropyl gold carbenes [J].

Amijs, Catelijne H. M. ;

Ferrer, Catalina ;

Echavarren, Antonio M. .

CHEMICAL COMMUNICATIONS, 2007, (07) :698-700

[2]

[Anonymous], ANGEW CHEM

[3]

BAE HJ, 2008, ANGEW CHEM, V120, P2295

[4] Gold(I)-catalyzed cycloisomerization of 3-methoxy-1,6-enynes featuring tandem cyclization and [3,3]-sigmatropic rearrangement [J].

Bae, Hyo J. ;

Baskar, Baburaj ;

An, Sang E. ;

Cheong, Jae Y. ;

Thangadurai, Daniel T. ;

Hwang, In-Chul ;

Rhee, Young H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2263-2266

[5] Gold-catalyzed intermolecular Hetero-Dehydro-Diels-Alder cycloaddition of captodative dienynes with nitriles:: A new reaction and regioselective direct access to pyridines [J].

Barluenga, Jose ;

Fernandez-Rodriguez, Manuel Angel ;

Garcia-Garcia, Patricia ;

Aguilar, Enrique .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (09) :2764-+

[6]

Bongers N., 2008, ANGEW CHEM, V120, P2208, DOI DOI 10.1002/ANGE.200704729

[7] Golden opportunities in stereoselective catalysis [J].

Bongers, Nadine ;

Krause, Norbert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) :2178-2181

[8]

Correa A., 2008, ANGEW CHEM, V120, P730

[9] Golden carousel in catalysis: The cationic gold/propargylic ester cycle [J].

Correa, Andrea ;

Marion, Nicolas ;

Fensterbank, Louis ;

Malacria, Max ;

Nolan, Steven P. ;

Cavallo, Luigi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (04) :718-721

[10] 1,2-alkyl migration as a key element in the invention of cascade reactions catalyzed by π-acids [J].

Crone, Benedikt ;

Kirsch, Stefan F. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (12) :3514-3522

← 1 2 3 4 5 →