Asymmetric 1,3-dipolar cycloaddition reaction between α,β-unsaturated aldehydes and nitrones catalyzed by well-defined iridium or rhodium catalysts

被引：37
|
作者：
Carmona, Daniel [1 ]
Lamata, M. Pilar [1 ]
Viguri, Fernando [1 ]
Rodriguez, Ricardo [1 ]
Fischer, Thomas [1 ]
Lahoz, Fernando J. [1 ]
Dobrinovitch, Isabel T. [1 ]
Oro, Luis A. [1 ]
机构：
[1] Univ Zaragoza, CSIC, Inst Ciencia Mat Aragon, Inst Univ Catalisis Homogenea,Dept Quim Inorgan, E-50009 Zaragoza, Spain
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 10期
关键词：
asymmetric catalysis; 1,3-dipolar cycloaddition reactions; enals; iridium; nitrones; rhodium;
D O I：
10.1002/adsc.200700010
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Reaction of the complexes (S-M,R-C)-[(eta(5)-C5Me5)M{(R)-Prophos}(H2O)](SbF6)(2) (M=Rh, Ir) with alpha,beta-unsaturated aldehydes diastereoselectively gave complexes (S-M,R-C)-[(eta(5)-C5Me5)M{(R)-Prophos}(enal)](SbF6)(2) which have been fully characterized, including an X-ray molecular structure determination of the complex (S-Rh,R-C)- [(eta(5)-C5Me5)Rh{(R)-Prophos)(trans-2-methyl-2-pentenal)](SbF6)(2). These enal complexes efficiently catalyze the enantioselective 1,3-dipolar cycloaddition of the nitrones N-benzylideneaniline N-oxide and 3,4-dihydroisoquinoline N-oxide to the corresponding enals. Reactions occur with excellent regioselectivity, perfect endo selectivity and with enantiomeric excesses up to 94%. The absolute configuration of the adduct 5-methyl-2,3-diphenylisoxazolidine-4-carboxaldehyde was determined through its (R)-(-)-alpha-methylbenzylamine derivative.
引用
收藏
页码：1751 / 1758
页数：8
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