Gold(I)-catalyzed divergence in the reactivity of 3-silyloxy 1,6-enynes: Pinacol-terminated vs claisen-terminated cyclization cascades

被引：66

作者：

Baskar, Baburaj ^{[1
]}

Bae, Hyo J. ^{[1
]}

An, Sang E. ^{[1
]}

Cheong, Jae Y. ^{[1
]}

Rhee, Young H. ^{[1
]}

Duschek, Alexander ^{[2
]}

Kirsch, Stefan F. ^{[2
]}

机构：

[1] POSTECH, Dept Chem, Pohang 790784, South Korea

[2] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 12期

关键词：

D O I：

10.1021/ol8008733

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

On activation with catalytic amounts of gold(I) complexes, 3-silyloxy 1,6-enynes can react through two alternative pathways. In one, a cascade reaction consisting of carbocyclization and subsequent pinacol rearrangement takes place. In the second pathway, a heterocyclization is followed by a Claisen rearrangement. The reaction outcome differs depending on the substitution pattern of the 3-silyloxy 1,6-enynes and, more importantly, the electronic properties of the gold-bound phosphane ligand.

引用

收藏

页码：2605 / 2607

页数：3

相关论文

共 44 条

[1] 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

[2] Gold- or platinum-catalyzed tandem cycloisomerization/Prins-type cyclization reactions [J].

Barluenga, J ;

Diéguez, A ;

Fernández, A ;

Rodríguez, F ;

Fañanás, FJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (13) :2091-2093

[3] Synthesis of heterocyclic systems by transition-metal-catalyzed cyclization migration reactions -: A diversity-oriented strategy for the construction of spirocyclic 3(2H)-furanones and 3-pyrrolones [J].

Binder, Jorg T. ;

Crone, Benedikt ;

Kirsch, Stefan F. ;

Liebert, Clemence ;

Menz, Helge .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (10) :1636-1647

[4] Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans [J].

Buzas, A ;

Istrate, F ;

Gagosz, F .

ORGANIC LETTERS, 2006, 8 (09) :1957-1959

[5] Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones [J].

Buzas, Andrea ;

Gagosz, Fabien .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12614-12615

[6] Gold(I)-catalyzed 5-endo hydroxy- and alkoxycyclization of 1,5-enynes:: Efficient access to functionalized cyclopentenes [J].

Buzas, Andrea K. ;

Istrate, Florin M. ;

Gagosz, Fabien .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1141-1144

[7] Diastereoselective gold-catalyzed cycloisomerizations of ene-ynamides [J].

Couty, Sylvain ;

Meyer, Christophe ;

Cossy, Janine .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (40) :6726-6730

[8] 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

[9] Synthesis of indenyl ethers by gold(I)-catalyzed intramolecular carboalkoxylation of alkynes [J].

Dube, Pascal ;

Toste, F. Dean .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (37) :12062-12063

[10] Metal-catalyzed [1,2]-alkyl shift in allenyl ketones: Synthesis of multisubstituted furans [J].

Dudnik, Alexander S. ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (27) :5195-5197

← 1 2 3 4 5 →