Axially Chiral Triazoloisoquinolin-3-ylidene Ligands in Gold(I)-Catalyzed Asymmetric Intermolecular (4+2) Cycloadditions of Allenamides and Dienes

被引:162
作者
Francos, Javier [2 ,3 ]
Grande-Carmona, Francisca [5 ]
Faustino, Helio [2 ,3 ]
Iglesias-Sigueenza, Javier [1 ]
Diez, Elena [1 ]
Alonso, Isaac [2 ,3 ]
Fernandez, Rosario [1 ]
Lassaletta, Jose M. [5 ]
Lopez, Fernando [4 ]
Mascarenas, Jose L. [2 ,3 ]
机构
[1] Univ Seville, Dept Quim Organ, E-41012 Seville, Spain
[2] Univ Santiago Compostela, Ctr Singular Invest Quim Biol & Mat Mol CIQUS, Santiago De Compostela 15782, Spain
[3] Univ Santiago Compostela, Dept Quim Organ, Unidad Asociada CSIC, Santiago De Compostela 15782, Spain
[4] Inst Quim Organ SIC, Madrid 28006, Spain
[5] Inst Invest Quim CSIC USe, Seville 41092, Spain
关键词
N-HETEROCYCLIC CARBENE; DIELS-ALDER REACTIONS; GOLD CATALYSIS; GRIGNARD-REAGENTS; COMPLEXES; ORGANOCATALYSIS; 1,6-ENYNES; TRANSFORMATION; ALLENEDIENES; DERIVATIVES;
D O I
10.1021/ja3065446
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first highly enantioselective intermolecular (4 + 2) cydoaddition between allenes and dienes is reported. The reaction provides good yields of optically active cyclohexenes featuring diverse substitution patterns and up to three stereocenters. Key to the success of the process is the use of newly designed axially chiral N-heterocyclic carbene-gold catalysts.
引用
收藏
页码:14322 / 14325
页数:4
相关论文
共 61 条
[1]   Imidazo[1,5-a]pyridine:: A versatile architecture for stable N-heterocyclic carbenes [J].
Alcarazo, M ;
Roseblade, SJ ;
Cowley, AR ;
Fernández, R ;
Brown, JM ;
Lassaletta, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3290-3291
[2]   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
[3]   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
[4]   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
[5]   New chiral ligands bearing two N-heterocyclic carbene moieties at a dioxolane backbone. Gold, palladium and rhodium complexes as enantioselective catalysts [J].
Arnanz, Avelina ;
Gonzalez-Arellano, Camino ;
Juan, Alberto ;
Villaverde, Gonzalo ;
Corma, Avelino ;
Iglesias, Marta ;
Sanchez, Felix .
CHEMICAL COMMUNICATIONS, 2010, 46 (17) :3001-3003
[6]   Catalytic amination of 2-substituted pyridines with hydrazine derivatives [J].
Arterburn, JB ;
Rao, KV ;
Ramdas, R ;
Dible, BR .
ORGANIC LETTERS, 2001, 3 (09) :1351-1354
[7]   Development of a Formal Catalytic Asymmetric [4+2] Addition of Ethyl-2,3-butadienoate with Acyclic Enones [J].
Ashtekar, Kumar Dilip ;
Staples, Richard J. ;
Borhan, Babak .
ORGANIC LETTERS, 2011, 13 (21) :5732-5735
[8]   Synthesis and Catalytic Activity of Gold Chiral Nitrogen Acyclic Carbenes and Gold Hydrogen Bonded Heterocyclic Carbenes in Cyclopropanation of Vinyl Arenes and in Intramolecular Hydroalkoxylation of Allenes [J].
Bartolome, Camino ;
Garcia-Cuadrado, Domingo ;
Ramiro, Zoraida ;
Espinet, Pablo .
INORGANIC CHEMISTRY, 2010, 49 (21) :9758-9764
[9]   Organocatalytic umpolung: N-heterocyclic carbenes and beyond [J].
Bugaut, Xavier ;
Glorius, Frank .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3511-3522
[10]   Imidazo[1,5-a]pyridine-3-ylidenes -: pyridine derived N-heterocyclic carbene ligands [J].
Burstein, C ;
Lehmann, CW ;
Glorius, F .
TETRAHEDRON, 2005, 61 (26) :6207-6217