C-2-SYMMETRICAL BIS(AZIRIDINES) - A NEW CLASS OF CHIRAL LIGANDS FOR TRANSITION METAL-MEDIATED ASYMMETRIC-SYNTHESIS

被引:92
作者
TANNER, D [1 ]
ANDERSSON, PG [1 ]
HARDEN, A [1 ]
SOMFAI, P [1 ]
机构
[1] LUND UNIV,LUND INST TECHNOL,S-22100 LUND,SWEDEN
关键词
CHIRAL LIGANDS; ASYMMETRIC DIHYDROXYLATION; CATALYTIC ASYMMETRIC ALLYLIC SUBSTITUTION; CATALYTIC ASYMMETRIC CYCLOPROPANATION; CATALYTIC ASYMMETRIC AZIRIDINATION;
D O I
10.1016/S0040-4039(00)60748-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The readily available C-2-symmetric bis(aziridines) I can act as ligands in a variety of asymmetric transformations mediated by transition metals In the best cases, > 95% ee can be obtained.
引用
收藏
页码:4631 / 4634
页数:4
相关论文
共 21 条
[1]   BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS [J].
EVANS, DA ;
WOERPEL, KA ;
HINMAN, MM ;
FAUL, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :726-728
[2]   BIS(OXAZOLINE) COPPER-COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS [J].
EVANS, DA ;
FAUL, MM ;
BILODEAU, MT ;
ANDERSON, BA ;
BARNES, DM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5328-5329
[3]   SEMICORRIN METAL-COMPLEXES AS ENANTIOSELECTIVE CATALYSTS .2. ENANTIOSELECTIVE CYCLOPROPANE FORMATION FROM OLEFINS WITH DIAZO-COMPOUNDS CATALYZED BY CHIRAL (SEMICORRINATO)COPPER COMPLEXES [J].
FRITSCHI, H ;
LEUTENEGGER, U ;
PFALTZ, A .
HELVETICA CHIMICA ACTA, 1988, 71 (06) :1553-1565
[4]   ASYMMETRIC DIHYDROXYLATION OF OLEFINS WITH A SIMPLE CHIRAL LIGAND [J].
HANESSIAN, S ;
MEFFRE, P ;
GIRARD, M ;
BEAUDOIN, S ;
SANCEAU, JY ;
BENNANI, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :1991-1993
[5]   ASYMMETRIC DIHYDROXYLATION VIA LIGAND-ACCELERATED CATALYSIS [J].
JACOBSEN, EN ;
MARKO, I ;
MUNGALL, WS ;
SCHRODER, G ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1968-1970
[6]  
JOHNSON RA, 1993, CATALYTIC ASYMMETRIC, P227
[7]   A SIMPLIFIED PROCEDURE FOR THE STEREOSPECIFIC TRANSFORMATION OF 1,2-DIOLS INTO EPOXIDES [J].
KOLB, HC ;
SHARPLESS, KB .
TETRAHEDRON, 1992, 48 (48) :10515-10530
[8]  
KUBOTA H, 1993, TETRAHEDRON, V50, P8135
[9]   5-AZA-SEMICORRINS - A NEW CLASS OF BIDENTATE NITROGEN LIGANDS FOR ENANTIOSELECTIVE CATALYSIS [J].
LEUTENEGGER, U ;
UMBRICHT, G ;
FAHRNI, C ;
VONMATT, P ;
PFALTZ, A .
TETRAHEDRON, 1992, 48 (11) :2143-2156
[10]   ASYMMETRIC ALKENE AZIRIDINATION WITH READILY AVAILABLE CHIRAL DIIMINE-BASED CATALYSTS [J].
LI, Z ;
CONSER, KR ;
JACOBSEN, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5326-5327