Enantioselective copper-catalyzed 1,3-dipolar cycloadditions

被引:783
作者
Stanley, Levi M. [1 ]
Sibi, Mukund P. [1 ]
机构
[1] N Dakota State Univ, Dept Chem & Mol Biol, Fargo, ND 58105 USA
关键词
D O I
10.1021/cr078371m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Scientists' achievements in the development of enantioselective copper-catalyzed 1,3-dipolar cycloaddition reactions have been summarized. Chiral copper catalysts have played an important role in this development. Noteworthy of this are the applications in aza-allyl type 1,3-dipoles such as nitrones, azomethine imines, and azomethine ylides.
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页码:2887 / 2902
页数:16
相关论文
共 105 条
[1]   CHIRAL CO(II) AND MN(II) CATALYSTS FOR THE 1,3-DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES DERIVED FROM ARYLIDENE IMINES OF GLYCINE [J].
ALLWAY, P ;
GRIGG, R .
TETRAHEDRON LETTERS, 1991, 32 (41) :5817-5820
[2]   L-proline-mediated one-pot synthesis of 3-exomethylene β-lactams via Kinugasa reaction [J].
Basak, A ;
Ghosh, SC .
SYNLETT, 2004, (09) :1637-1639
[3]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[4]   Asymmetric 1,3-dipolar cycloadditions of cyclic stabilized ylides derived from chiral 1,2-amino alcohols [J].
Bonin, Martine ;
Chauveau, Ariane ;
Micouin, L. .
SYNLETT, 2006, (15) :2349-2363
[5]  
Bruggink A, 2001, SYNTHESIS OF BETA-LACTAM ANTIBIOTICS: CHEMISTRY, BIOCATALYSIS & PROCESS INTEGRATION, P12
[6]   Highly enantioselective copper(I)-fesulphos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides [J].
Cabrera, S ;
Arrayás, RG ;
Carretero, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16394-16395
[7]   CuI-fesulphos complexes:: efficient chiral catalysts for asymmetric 1,3-dipolar cycloaddition of azomethine ylides [J].
Cabrera, Silvia ;
Arrayas, Ramon Gomez ;
Martin-Matute, Belen ;
Cossio, Fernando P. ;
Carretero, Juan C. .
TETRAHEDRON, 2007, 63 (28) :6587-6602
[8]   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
[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]   Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis [J].
Chen, C ;
Li, XD ;
Schreiber, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10174-10175