Gold(I)-Catalyzed Intermolecular [2+2]Cycloadditions between Allenamides and Alkenes

被引:99
作者
Faustino, Helio [2 ]
Bernal, Paloma [2 ]
Castedo, Luis [2 ]
Lopez, Fernando [1 ]
Mascarenas, Jose L. [2 ]
机构
[1] CSIC, Inst Quim Organ, Madrid 28006, Spain
[2] Univ Santiago de Compostela, Dept Quim Organ, Ctr Singular Invest Quim Biol & Mat Mol, Unidad Asociada CSIC, Santiago De Compostela 15782, Spain
关键词
allenamides; cycloaddition; cyclobutanes; enamides; gold; 4+3 CYCLOADDITION REACTIONS; GOLD CATALYSIS; INTRAMOLECULAR CYCLOADDITION; ORGANIC-SYNTHESIS; ALLYL CATIONS; ACCESS; ALLENEDIENES; ALLENES; DIENES; 4C+3C;
D O I
10.1002/adsc.201200047
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
3-(Propa-1,2-dien-1-yl)oxazolidin-2-one works as an efficient two-carbon partner in a variety of intermolecular gold-catalyzed [2+2]?cycloadditions to alkenes. The transformation represents a simple and practical entry to highly substituted cyclobutane derivatives and takes place with complete regio- and stereocontrol.
引用
收藏
页码:1658 / 1664
页数:7
相关论文
共 52 条
[1]   Exploiting [2+2] cycloaddition chemistry: achievements with allenes [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :783-816
[2]  
Alcarazo M., 2010, ANGEW CHEM, V122, P2596
[3]   Steering the Surprisingly Modular π-Acceptor Properties of N-Heterocyclic Carbenes: Implications for Gold Catalysis [J].
Alcarazo, Manuel ;
Stork, Timon ;
Anoop, Anakuthil ;
Thiel, Walter ;
Fuerstner, Alois .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (14) :2542-2546
[4]  
Alonso I., 2011, ANGEW CHEM, V123, P11698
[5]   Enantioselective Gold(I)-Catalyzed Intramolecular (4+3) Cycloadditions of Allenedienes [J].
Alonso, Isaac ;
Faustino, Helio ;
Lopez, Fernando ;
Mascarenas, Jose L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) :11496-11500
[6]   Gold-Catalyzed [4C+2C] Cycloadditions of Allenedienes, including an Enantioselective Version with New Phosphoramidite-Based Catalysts: Mechanistic Aspects of the Divergence between [4C+3C] and [4C+2C] Pathways [J].
Alonso, Isaac ;
Trillo, Beatriz ;
Lopez, Fernando ;
Montserrat, Sergi ;
Ujaque, Gregori ;
Castedo, Luis ;
Lledos, Agusti ;
Mascarenas, Jose L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) :13020-13030
[7]   Alternative synthetic methods through new developments in catalysis by gold [J].
Arcadi, Antonio .
CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325
[8]   On the Impact of Steric and Electronic Properties of Ligands on Gold(I)-Catalyzed Cycloaddition Reactions [J].
Benitez, Diego ;
Tkatchouk, Ekaterina ;
Gonzalez, Ana Z. ;
Goddard, William A., III ;
Toste, F. Dean .
ORGANIC LETTERS, 2009, 11 (21) :4798-4801
[9]   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
[10]   Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions [J].
Corma, A. ;
Leyva-Perez, A. ;
Sabater, Maria J. .
CHEMICAL REVIEWS, 2011, 111 (03) :1657-1712