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
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页码:3391 / 3394
页数:4
相关论文
共 17 条
  • [1] A NEW COORDINATING CHIRAL LITHIUM AMIDE
    BARR, D
    BERRISFORD, DJ
    JONES, RVH
    SLAWIN, AMZ
    SNAITH, R
    STODDART, JF
    WILLIAMS, DJ
    [J]. 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
    COREY, EJ
    JARDINE, PD
    VIRGIL, S
    YUEN, PW
    CONNELL, RD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) : 9243 - 9244
  • [3] ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES
    COX, PJ
    SIMPKINS, NS
    [J]. 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
    DIECK, HT
    DIETRICH, J
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1984, 117 (02): : 694 - 701
  • [5] ON ENANTIOSELECTIVE DEPROTONATION - SYNTHESIS AND CRYSTAL-STRUCTURE OF A CHIRAL AMIDOLITHIUM TETRAHYDROFURAN COMPLEX
    EDWARDS, AJ
    HOCKEY, S
    MAIR, FS
    RAITHBY, PR
    SNAITH, R
    SIMPKINS, NS
    [J]. 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
    ELEVELD, MB
    HOGEVEEN, H
    SCHUDDE, EP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) : 3635 - 3642
  • [7] ASYMMETRIC DIHYDROXYLATION OF OLEFINS WITH A SIMPLE CHIRAL LIGAND
    HANESSIAN, S
    MEFFRE, P
    GIRARD, M
    BEAUDOIN, S
    SANCEAU, JY
    BENNANI, Y
    [J]. 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
    NAKAJIMA, M
    TOMIOKA, K
    KOGA, K
    [J]. TETRAHEDRON, 1993, 49 (43) : 9735 - 9750
  • [10] AN ENANTIOSELECTIVE SYNTHESIS OF VICINAL DIAMINES
    NANTZ, MH
    LEE, DA
    BENDER, DM
    ROOHI, AH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) : 6653 - 6657