Iridium-Catalyzed 1,3-Dipolar Cycloadditions

被引:4
作者
Carmona, Daniel [1 ]
Oro, Luis A. [1 ]
机构
[1] Univ Zaragoza, Inst Ciencia Mat Aragon, CSIC, E-50009 Zaragoza, Spain
来源
IRIDIUM CATALYSIS | 2011年 / 34卷
关键词
1,3-Dipolar cycloadditions; Enals; Iridium catalysts; Methacrylonitrile; Nitrones; LEWIS-ACID; ALPHA; BETA-UNSATURATED ALDEHYDES; NITRONE CYCLOADDITION; RUTHENIUM COMPLEXES; RHODIUM; REACTIVITY; ALKENES; REGIOSELECTIVITY; SUBSTITUENT; MECHANISM;
D O I
10.1007/978-3-642-15334-1_8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
1,3-Dipolar cycloaddition reactions (DCR) are atom-economic processes that permit the construction of heterocycles. Their enantioselective versions allow for the creation of up to four adjacent chiral centers in a concerted fashion. In particular, well-defined half-sandwich iridium (III) catalysts have been applied to the DCR between enals or methacrylonitrile with nitrones. Excellent yield and stereoselectivities have been achieved. Support for mechanistic proposals stems from the isolation and characterization of the true catalysts.
引用
收藏
页码:209 / 229
页数:21
相关论文
共 47 条
[1]  
ALI SA, 1988, TETRAHEDRON, V44, P5911
[2]  
[Anonymous], 1 3 DIPOLAR CYCLOADD
[3]  
[Anonymous], 1 3 DIPOLAR CYCLOADD
[4]  
Badoiu A, 2008, CHEM-ASIAN J, V3, P1298, DOI [10.1002/asia.200800063, 10.1002/asia.200990022]
[5]   Asymmetric Lewis acid-catalyzed 1,3-dipolar cycloadditions [J].
Badoiu, Andrei ;
Brinkmann, Yasmin ;
Viton, Florian ;
Kuendig, E. Peter .
PURE AND APPLIED CHEMISTRY, 2008, 80 (05) :1013-1018
[6]   Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids [J].
Brandi, Alberto ;
Cardona, Francesca ;
Cicchi, Stefano ;
Cordero, Franca M. ;
Goti, Andrea .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (32) :7808-7821
[7]  
Brunner H, 2001, EUR J INORG CHEM, P905
[8]   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
[9]   Chiral ruthenium complexes as catalysts in enantioselective Diels-Alder reactions. Crystal structure of the Lewis acid dienophile adduct [J].
Carmona, D ;
Cativiela, C ;
Elipe, S ;
Lahoz, FJ ;
Lamata, MP ;
Pilar, M ;
de Viu, LR ;
Oro, LA ;
Vega, C ;
Viguri, F .
CHEMICAL COMMUNICATIONS, 1997, (24) :2351-2352
[10]   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