Asymmetric Lewis acid-catalyzed 1,3-dipolar cycloadditions

被引:33
作者
Badoiu, Andrei [1 ]
Brinkmann, Yasmin [1 ]
Viton, Florian [1 ]
Kuendig, E. Peter [1 ]
机构
[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland
关键词
lewis acids; asymmetric reactions; 1,3-dipolar cycloadditions; nitrones; nitrile oxides;
D O I
10.1351/pac200880051013
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Highly tuned, one-point binding chiral iron and ruthenium complexes selectively coordinate and activate alpha,beta-unsaturated aldehydes and ketones toward asymmetric catalytic Diels-Alder cycloaddition reactions. Here we focus on the application of these transition-metal Lewis acids to asymmetric catalytic 1,3-dipolar cycloaddition reaction between enals and cyclic and acyclic nitrones as well as aryl nitrile oxides to give isoxazolidines and isoxazolines, respectively.
引用
收藏
页码:1013 / 1018
页数:6
相关论文
共 49 条
[1]   [CpRu((R)-Binop-F)(H2O)][SbF6], a new fluxional chiral lewis acid catalyst:: Synthesis, dynamic NMR, asymmetric catalysis, and theoretical studies [J].
Alezra, V ;
Bernardinelli, G ;
Corminboeuf, C ;
Frey, U ;
Kündig, EP ;
Merbach, AE ;
Saudan, CM ;
Viton, F ;
Weber, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (15) :4843-4853
[2]  
[Anonymous], CYCLOADDITION REACTI
[3]  
BADOIU A, 2008, IN PRESS CHEM ASIAN
[4]   Chiral ruthenium Lewis acid-catalyzed nitrile oxide cycloadditions [J].
Brinkmann, Yasmin ;
Madhushaw, Reniguntala J. ;
Jazzar, Rodolphe ;
Bernardinelli, Gerald ;
Kuendig, E. Peter .
TETRAHEDRON, 2007, 63 (35) :8413-8419
[5]   A new chiral ligand for the Fe-Lewis acid catalysed asymmetric Diels-Alder reaction [J].
Bruin, ME ;
Kundig, EP .
CHEMICAL COMMUNICATIONS, 1998, (23) :2635-2636
[6]   The complete characterization of a rhodium Lewis acid-dipolarophile complex as an intermediate for the enantioselective catalytic 1,3-dipolar cycloaddition of C,N-diphenylnitrone to methacrolein [J].
Carmona, D ;
Lamata, MP ;
Viguri, F ;
Rodríguez, R ;
Oro, LA ;
Balana, AI ;
Lahoz, FJ ;
Tejero, T ;
Merino, P ;
Franco, S ;
Montesa, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (09) :2716-2717
[7]   Enantioselective 1,3-dipolar cycloaddition of nitrones to methacrolein catalyzed by (η5-C5Me5)M{(R)-Prophos} containing complexes (M = Rh, Ir;: (R)-Prophos=1,2-bis(diphenylphosphino)propane):: On the origin of the enantioselectivity [J].
Carmona, D ;
Lamata, MP ;
Viguri, F ;
Rodríguez, R ;
Oro, LA ;
Lahoz, FJ ;
Balana, AI ;
Tejero, T ;
Merino, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13386-13398
[8]   Half-sandwich rhodium (and iridium) complexes as enantioselective catalysts for the 1,3-dipolar cycloaddition of 3,4-dihydroisoquinoline n-oxide to methacrylonitrile [J].
Carmona, Daniel ;
Lamata, M. Pilar ;
Viguri, Fernando ;
Rodriguez, Ricardo ;
Lahoz, Fernando J. ;
Oro, Luis A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (35) :9746-9756
[9]   Asymmetric 1,3-dipolar cycloaddition reaction between α,β-unsaturated aldehydes and nitrones catalyzed by well-defined iridium or rhodium catalysts [J].
Carmona, Daniel ;
Lamata, M. Pilar ;
Viguri, Fernando ;
Rodriguez, Ricardo ;
Fischer, Thomas ;
Lahoz, Fernando J. ;
Dobrinovitch, Isabel T. ;
Oro, Luis A. .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (10) :1751-1758
[10]   Chiral half-sandwich ruthenium(II) complexes as catalysts in 1,3-dipolar cycloaddition reactions of nitrones with methacrolein [J].
Carmona, Daniel ;
Lamata, M. Pilar ;
Viguri, Fernando ;
Ferrer, Joaquina ;
Garcia, Nestor ;
Lahoz, Fernando J. ;
Martin, M. Luisa ;
Oro, Luis A. .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2006, (16) :3155-3166