SIMPLE SYNTHESIS OF A C-2 SYMMETRICAL VICINAL DIAMINE - HIGHLY DIASTEREOSELECTIVE GRIGNARD ADDITION TO A CHIRAL BIS-IMINE

被引:95
作者
BAMBRIDGE, K [1 ]
BEGLEY, MJ [1 ]
SIMPKINS, NS [1 ]
机构
[1] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)76916-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of the enantiomerically pure bis-imine derived from glyoxal and (R)-alpha-methylbenzylamine with PhMgCl in diethylether is highly diastereoselective, resulting in the selective formation of the C-2 symmetric vicinal diamine 7.
引用
收藏
页码:3391 / 3394
页数:4
相关论文
共 17 条
[1]   A NEW COORDINATING CHIRAL LITHIUM AMIDE [J].
BARR, D ;
BERRISFORD, DJ ;
JONES, RVH ;
SLAWIN, AMZ ;
SNAITH, R ;
STODDART, JF ;
WILLIAMS, DJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (08) :1044-1047
[2]   ENANTIOSELECTIVE VICINAL HYDROXYLATION OF TERMINAL AND E-1,2-DISUBSTITUTED OLEFINS BY A CHIRAL COMPLEX OF OSMIUM TETRAOXIDE - AN EFFECTIVE CONTROLLER SYSTEM AND A RATIONAL MECHANISTIC MODEL [J].
COREY, EJ ;
JARDINE, PD ;
VIRGIL, S ;
YUEN, PW ;
CONNELL, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9243-9244
[3]   ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES [J].
COX, PJ ;
SIMPKINS, NS .
TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :1-26
[4]   DIAZADIENES AS CONTROLLING LIGANDS IN CATALYSIS .5. SYNTHESIS OF CHIRAL DIAZADIENES R]-N=CR'-CR'=N-R [J].
DIECK, HT ;
DIETRICH, J .
CHEMISCHE BERICHTE-RECUEIL, 1984, 117 (02) :694-701
[5]   ON ENANTIOSELECTIVE DEPROTONATION - SYNTHESIS AND CRYSTAL-STRUCTURE OF A CHIRAL AMIDOLITHIUM TETRAHYDROFURAN COMPLEX [J].
EDWARDS, AJ ;
HOCKEY, S ;
MAIR, FS ;
RAITHBY, PR ;
SNAITH, R ;
SIMPKINS, NS .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :6942-6943
[6]   DIASTEREOSELECTIVE SYNTHESIS OF CHIRAL SECONDARY-AMINES WITH 2 CHIRAL CENTERS DIRECTLY ATTACHED TO THE NITROGEN ATOM [J].
ELEVELD, MB ;
HOGEVEEN, H ;
SCHUDDE, EP .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3635-3642
[7]   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
[8]  
HORNER L, 1984, LIEBIGS ANN CHEM, P1240
[9]   DESIGN AND SYNTHESIS OF NOVEL CHIRAL PYRROLIDINE-BASED DIAMINES WITH C(2)-SYMMETRY [J].
NAKAJIMA, M ;
TOMIOKA, K ;
KOGA, K .
TETRAHEDRON, 1993, 49 (43) :9735-9750
[10]   AN ENANTIOSELECTIVE SYNTHESIS OF VICINAL DIAMINES [J].
NANTZ, MH ;
LEE, DA ;
BENDER, DM ;
ROOHI, AH .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6653-6657