Stereoselective intramolecular cyclopropanation through catalytic olefin activation

被引:63
作者
Huang, Xueliang [1 ]
Klimczyk, Sebastian [1 ]
Veiros, Luis F. [2 ]
Maulide, Nuno [1 ]
机构
[1] Max Planck Inst Kohlenforsch, Mulheim, Germany
[2] Univ Tecn Lisboa, Ctr Quim Estrutural, Inst Super Tecn, P-1049001 Lisbon, Portugal
关键词
ALPHA-AMINO-ACIDS; OXIDATIVE CYCLIZATION; UNACTIVATED ALKENES; NATURAL OCCURRENCE; EFFICIENT ACCESS; CARBENE-TRANSFER; GOLD; HYDROAMINATION; CYCLOISOMERIZATION; COMPLEXES;
D O I
10.1039/c2sc21914j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel stereoselective and convergent catalytic method for the cyclopropanation of electron-neutral and -rich olefins by sulfonium ylides is reported which unusually proceeds through olefin activation rather than by metal carbene formation.
引用
收藏
页码:1105 / 1110
页数:6
相关论文
共 96 条
[21]   Recent advances in asymmetric catalytic metal carbene transformations [J].
Doyle, MP ;
Forbes, DC .
CHEMICAL REVIEWS, 1998, 98 (02) :911-935
[22]   CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].
DOYLE, MP .
CHEMICAL REVIEWS, 1986, 86 (05) :919-939
[23]   Potential Energy Surface for (Retro-)Cyclopropanation: Metathesis with a Cationic Gold Complex [J].
Fedorov, Alexey ;
Batiste, Laurent ;
Bach, Andreas ;
Birney, David M. ;
Chen, Peter .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (31) :12162-12171
[24]   A gold catalyst for carbene-transfer reactions from ethyl diazoacetate [J].
Fructos, MR ;
Belderrain, TR ;
de Frémont, P ;
Scott, NM ;
Nolan, SP ;
Díaz-Requejo, MM ;
Pérez, PJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5284-5288
[25]   Catalytic carbophilic activation:: Catalysis by platinum and gold π acids [J].
Fuerstner, Alois ;
Davies, Paul W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) :3410-3449
[26]   Gold and platinum catalysis-a convenient tool for generating molecular complexity [J].
Fuerstner, Alois .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3208-3221
[27]   Ligand effects in homogeneous Au catalysis [J].
Gorin, David J. ;
Sherry, Benjamin D. ;
Toste, F. Dean .
CHEMICAL REVIEWS, 2008, 108 (08) :3351-3378
[28]   Relativistic effects in homogeneous gold catalysis [J].
Gorin, David J. ;
Toste, F. Dean .
NATURE, 2007, 446 (7134) :395-403
[29]   Gold(I)-catalyzed intramolecular hydroamination of alkenyl carbamates [J].
Han, XQ ;
Widenhoefer, RA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (11) :1747-1749
[30]   Gold-catalyzed organic reactions [J].
Hashmi, A. Stephen K. .
CHEMICAL REVIEWS, 2007, 107 (07) :3180-3211