HIGHLY ENANTIOSELECTIVE ALDOL REACTION MEDIATED BY MIXED AGGREGATES DERIVED FROM A LITHIUM ESTER ENOLATE AND TETRADENTATE CHIRAL LITHIUM AMIDES

被引:27
作者
URAGAMI, M [1 ]
TOMIOKA, K [1 ]
KOGA, K [1 ]
机构
[1] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN
关键词
D O I
10.1016/0957-4166(95)00066-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A highly enantioselective aldol addition reaction between a lithium ester enolate with aldehydes has been achieved in up to 96% ee for anti products by using tetradentate chiral lithium amides (2c, 2d) that are designed to form heterodimeric mixed aggregates with a lithium enolate,
引用
收藏
页码:701 / 704
页数:4
相关论文
共 17 条
[1]   ENANTIOSELECTIVE ALDOL REACTIONS USING CHIRAL LITHIUM AMIDES AS A CHIRAL AUXILIARY [J].
ANDO, A ;
SHIOIRI, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) :1620-1621
[2]  
CHOY W, 1981, J AM CHEM SOC, V103, P1566
[3]   THE E/Z GEOMETRY OF THE ENOLATE COMPONENT DETERMINES FACE SELECTION OF THE ALDEHYDE COMPONENT IN CHIRAL DIAZABOROLIDINE-DIRECTED ENANTIOSELECTIVE ALDOL COUPLING [J].
COREY, EJ ;
LEE, DH .
TETRAHEDRON LETTERS, 1993, 34 (11) :1737-1740
[4]   VERSATILE CHIRAL REAGENT FOR THE HIGHLY ENANTIOSELECTIVE SYNTHESIS OF EITHER ANTI OR SYN ESTER ALDOLS [J].
COREY, EJ ;
KIM, SS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4976-4977
[5]  
EVANS DA, 1982, TOP STEREOCHEM, V13, P1, DOI DOI 10.1002/9780470147221.CHL
[6]   CATALYTIC ASYMMETRIC ALDOL REACTIONS - USE OF A CHIRAL (ACYLOXY)BORANE COMPLEX AS A VERSATILE LEWIS ACID CATALYST [J].
FURUTA, K ;
MARUYAMA, T ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1041-1042
[7]  
HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, P111
[8]   CATALYTIC ASYMMETRIC BENZYLATION OF ACHIRAL LITHIUM ENOLATES USING A CHIRAL LIGAND FOR LITHIUM IN THE PRESENCE OF AN ACHIRAL LIGAND [J].
IMAI, M ;
HAGIHARA, A ;
KAWASAKI, H ;
MANABE, K ;
KOGA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8829-8830
[9]   ENANTIOSELECTIVE CROSS ALDOL REACTION VIA DIVALENT TIN ENOLATE [J].
IWASAWA, N ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1982, (09) :1441-1444
[10]  
JUARISTI E, 1993, SYNTHESIS-STUTTGART, P1271