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

被引:182
作者
Crone, Benedikt [1 ]
Kirsch, Stefan F. [1 ]
机构
[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany
关键词
cascade reactions; catalysis; gold; platinum; rearrangement;
D O I
10.1002/chem.200701985
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This brief overview highlights recent progress in the field of cascade reactions that are initiated by the activation of a pi-system using platinum and gold catalysts and that are coupled with a 1,2-alkyl migration step. While the reactions discussed aim to rapidly evolve molecular complexity, they are experimentally straightforward and easy to perform. Primarily guided by the type of 1,2-alkyl migration, methods are categorized as shifts to metal carbenoid centers and pinacol-type rearrangements.
引用
收藏
页码:3514 / 3522
页数:9
相关论文
共 123 条
[1]  
[Anonymous], 2005, ANGEW CHEM, V117, P7150, DOI DOI 10.1002/ANGE.200502735
[2]  
[Anonymous], 2007, ANGEW CHEM, V119, P1159
[3]   Recent applications of gold catalysis in organic synthesis [J].
Arcadi, A ;
Di Giuseppe, S .
CURRENT ORGANIC CHEMISTRY, 2004, 8 (09) :795-812
[4]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[5]   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
[6]  
BARLUENGA J, 2006, ANGEW CHEM, V118, P2145
[7]   Gold-catalyzed tandem cycloisomerization-hydroalkoxylation of homopropargylic alcohols [J].
Belting, Volker ;
Krause, Norbert .
ORGANIC LETTERS, 2006, 8 (20) :4489-4492
[8]   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
[9]   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
[10]   Stereoselection in the prins-pinacol synthesis of acyltetrahydrofurans [J].
Cohen, F ;
MacMillan, DWC ;
Overman, LE ;
Romero, A .
ORGANIC LETTERS, 2001, 3 (08) :1225-1228