N-Heterocyclic Carbene Catalyzed Domino Reactions

被引:895
作者
Grossmann, Andre [1 ]
Enders, Dieter [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
asymmetric catalysis; carbenes; domino reactions; organocatalysis; umpolung; STETTER-ALDOL-MICHAEL; ALPHA; BETA-UNSATURATED ALDEHYDES; FORMYLCYCLOPROPANE 1,1-DIESTERS; STEREOSELECTIVE-SYNTHESIS; ORGANOCATALYTIC SYNTHESIS; OXIDATIVE ESTERIFICATION; NUCLEOPHILIC CARBENES; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITIONS; RING EXPANSION;
D O I
10.1002/anie.201105415
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
While organocatalyzed domino reactions or organocascade catalysis developed into an important tool in synthetic chemistry during the past decade, the utility of N-heterocyclic carbenes (NHCs) as catalysts in domino reactions has only received growing attention in the past three years. Taking into account the unique activation modes of the substrates by NHC catalysts, it is often difficult to distinguish between a single chemical transformation and a sequential one-pot transformation. Therefore, herein we present a critical consideration of domino, cascade, and tandem catalysis in the case of NHC catalysts and highlight recent publications in this area.
引用
收藏
页码:314 / 325
页数:12
相关论文
共 141 条
[1]   Direct organocatalytic synthesis of enantiopure succinimides from β-lactam aldehydes through ring expansion promoted by azolium salt precatalysts [J].
Alcaide, Benito ;
Almendros, Pedro ;
Cabrero, Gema ;
Ruiz, M. Pilar .
CHEMICAL COMMUNICATIONS, 2007, (45) :4788-4790
[2]   Formation and stability of N-heterocyclic carbenes in water:: The carbon acid pKa of imidazollum cations in aqueous solution [J].
Amyes, TL ;
Diver, ST ;
Richard, JP ;
Rivas, FM ;
Toth, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4366-4374
[3]  
[Anonymous], 2011, ANGEW CHEM
[4]  
[Anonymous], 2011, ANGEW CHEM
[5]  
[Anonymous], 2004, ANGEW CHEM
[6]   Looking for stable carbenes: The difficulty in starting anew [J].
Arduengo, AJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (11) :913-921
[7]   Organocatalytic Formation of Quaternary Stereocenters [J].
Bella, Marco ;
Gasperi, Tecla .
SYNTHESIS-STUTTGART, 2009, (10) :1583-1614
[8]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[9]   Organocatalysis-after the gold rush [J].
Bertelsen, Soren ;
Jorgensen, Karl Anker .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189
[10]  
Biju A.T., 2010, Angew. Chem, V122, P9955