Stereochemical diversity in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides

被引：130
作者：
Adrio, Javier [1 ,2 ]
Carretero, Juan C. [1 ,2 ]
机构：
[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain
[2] Univ Autonoma Madrid, Inst Adv Res Chem Sci IAdChem, E-28049 Madrid, Spain
来源：
CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 80期
关键词：
SELECTIVE 3+2 CYCLOADDITION; NON-BIARYL ATROPISOMERS; ENANTIOSELECTIVE SYNTHESIS; CHIRAL CATALYSTS; COMPLEXES; CONSTRUCTION; DIASTEREO; PROLINE; ACCESS; DERIVATIVES;
D O I：
10.1039/c9cc05238k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The pyrrolidine ring is a privileged structural motif in synthetic and medicinal chemisty. This review aims to highlight the high versatility of the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides for access to different types of stereochemical patterns in enantioselective pyrrolidine synthesis. Special attention will be paid to stereodivergent procedures giving rise to different stereoisomers from the same starting materials.
引用
收藏
页码：11979 / 11991
页数：13
相关论文
共 124 条
[71]   Hierarchical Selectivity in Fullerenes: Site-, Regio-, Diastereo-, and Enantiocontrol of the 1,3-Dipolar Cycloaddition to C70 [J].
Maroto, Enrique E. ;
de Cozar, Abel ;
Filippone, Salvatore ;
Martin-Domenech, Angel ;
Suarez, Margarita ;
Cossio, Fernando P. ;
Martin, Nazario .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) :6060-6064
[72]   BINAP-AgSbF6 vs. BINAP-AgClO4 Complexes as Catalysts for the Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides and Alkenes [J].
Martin-Rodrigues, Maria ;
Najera, Carmen ;
Sansano, Jose M. ;
Costa, Paulo R. R. ;
de Lima, Evanoel Crizanto ;
Dias, Ayres G. .
SYNLETT, 2010, (06) :962-966
[73]   Binap-Gold(I) versus Binap-Silver Trifluoroacetate Complexes as Catalysts in 1,3-Dipolar Cycloadditions of Azomethine Ylides [J].
Martin-Rodriguez, Maria ;
Najera, Carmen ;
Sansano, Jose M. ;
de Cozar, Abel ;
Cossio, Fernando P. .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (50) :14224-14233
[74]   Indolizidine and quinolizidine alkaloids [J].
Michael, Joseph P. .
NATURAL PRODUCT REPORTS, 2008, 25 (01) :139-165
[75]  
Mukaiyama T., 1985, ORGANIC CHEM TRENDS, V127
[76]   Catalytic enantioselective 1,3-dipolar cycloaddition reaction of azomethine ylides and alkenes:: The direct strategy to prepare enantioenriched highly substituted proline derivatives [J].
Nájera, C ;
Sansano, JM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (39) :6272-6276
[77]  
Najera C., 2014, J ORGANOMET CHEM, P771
[78]   Catalytic enantioselective 1,3-dipolar cycloaddition reactions of azomethine ylides and alkenes by using phosphoramidite-silver(I) complexes [J].
Najera, Carmen ;
Retamosa, M. de Gracia ;
Sansano, Jose M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (32) :6055-6058
[79]   Metal Complexes versus Organocatalysts in Asymmetric 1,3-Dipolar Cycloadditions [J].
Najera, Carmen ;
Sansano, Jose M. ;
Yus, Miguel .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2010, 21 (03) :377-412
[80]   Synthesis of Prolines by Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides and Alkenes Catalyzed by Chiral Phosphoramidite-Silver(I) Complexes [J].
Najera, Carmen ;
de Gracia Retamosa, Maria ;
Martin-Rodriguez, Maria ;
Sansano, Jose M. ;
de Cozar, Abel ;
Cossio, Fernando P. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (32) :5622-5634
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