A chiral molecular recognition approach to the formation of optically active quaternary centres in aza-Henry reactions

被引:129
作者
Knudsen, KR [1 ]
Jorgensen, KA [1 ]
机构
[1] Aarhus Univ, Danish Natl Res Fdn, Ctr Catalysis, Dept Chem, DK-8000 Aarhus, Denmark
关键词
D O I
10.1039/b500618j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An approach to asymmetric catalysis based on chiral molecular recognition by the combination of chiral Lewis acids and chiral organocatalysis for the formation of optically active quarternary centers in the aza-Henry reaction is presented; this procedure leads to products with up to 98% ee and a diastereomeric ratio of 14 : 1 in excellent yields with catalyst loadings of 5 mol%.
引用
收藏
页码:1362 / 1364
页数:3
相关论文
共 30 条
[1]   The nitro-Mannich reaction and its application to the stereoselective synthesis of 1,2-diamines [J].
Adams, H ;
Anderson, JC ;
Peace, S ;
Pennell, AMK .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9932-9934
[2]  
Anderson JC, 2000, SYNLETT, P850
[3]   Self-assembly of heterobimetallic complexes and reactive nucleophiles: A general strategy for the activation of asymmetric reactions promoted by heterobimetallic catalysts [J].
Arai, T ;
Yamada, YMA ;
Yamamoto, N ;
Sasai, H ;
Shibasaki, M .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (11) :1368-1372
[4]  
Baer H. H., 1970, CHEM NITRO NITROSO 2, P117
[5]   Asymmetric alcoholysis of cyclic anhydrides [J].
Chen, YG ;
McDaid, P ;
Deng, L .
CHEMICAL REVIEWS, 2003, 103 (08) :2965-2983
[6]  
Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[7]  
2-V
[8]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[9]  
2-V
[10]   Nucleophilic chiral amines as catalysts in asymmetric synthesis [J].
France, S ;
Guerin, DJ ;
Miller, SJ ;
Lectka, T .
CHEMICAL REVIEWS, 2003, 103 (08) :2985-3012