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
[91]   Theoretical chemistry of gold [J].
Pyykkö, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (34) :4412-4456
[92]  
Pyykko P., 2004, ANGEW CHEM, V116, P4512
[93]   DIOXOPYRROLINES .31. 2-AZABICYCLO[3.2.0]HEPTANE-3,4-DIONE (8) - A NOVEL ACID-CATALYZED SKELETAL REARRANGEMENT OF 7-OXY-7-VINYL DERIVATIVES TO 2-AZATRICYCLO[4.3.0.0.4,9]NONANE-3,7-DIONES [J].
SANO, T ;
TODA, J ;
TSUDA, Y .
HETEROCYCLES, 1984, 22 (01) :53-58
[94]   Efficient method for synthesis of angucyclinone antibiotics via gold-catalyzed intramolecular [4+2] benzannulation:: Enantioselective total synthesis of (+)-ochromycinone and (+)-rubiginone B2 [J].
Sato, K ;
Asao, N ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22) :8977-8981
[95]   1,2-Vinyl and 1,2-acetylenyl migration in Rh(II) carbene reaction: Remarkable bystander effect [J].
Shi, WF ;
Xiao, FP ;
Wang, JB .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (11) :4318-4322
[96]   Ga(III)-catalyzed cycloisomerization strategy for the synthesis of icetexane diterpenoids:: Total synthesis of (±)-salviasperanol [J].
Simmons, Eric M. ;
Sarpong, Richmond .
ORGANIC LETTERS, 2006, 8 (13) :2883-2886
[97]   Pt-catalyzed cyclization/1,2-migration for the synthesis of indolizines, pyrrolones, and indolizinones [J].
Smith, Cameron R. ;
Bunnelle, Eric M. ;
Rhodes, Allison J. ;
Sarpong, Richmond .
ORGANIC LETTERS, 2007, 9 (06) :1169-1171
[98]  
Staben S. T., 2006, ANGEW CHEM, V118, P6137
[99]   Gold(I)-catalyzed cyclizations of silyl enol ethers: Application to the synthesis of (+)-lycopladine A [J].
Staben, Steven T. ;
Kennedy-Smith, Joshua J. ;
Huang, David ;
Corkey, Britton K. ;
LaLonde, Rebecca L. ;
Toste, F. Dean .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (36) :5991-5994
[100]   Au- and Pt-catalyzed cycloisomerizations of 1,5-enynes to cyclohexadienes with a broad alkyne scope [J].
Sun, Jianwei ;
Conley, Matthew P. ;
Zhang, Liming ;
Kozmin, Sergey A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) :9705-9710