alpha-Lithiation of N-(tert-butoxycarbonyl)-N-(p-methoxyphenyl)allylamines mediated by (-)-sparteine: Enantioselective syntheses of either enantiomer of 3-substituted enecarbamates

被引:84
作者
Weisenburger, GA [1 ]
Beak, P [1 ]
机构
[1] UNIV ILLINOIS,DEPT CHEM,URBANA,IL 61801
关键词
D O I
10.1021/ja962793o
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
[No abstract available]
引用
收藏
页码:12218 / 12219
页数:2
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共 17 条
  • [1] CHIRAL HOMOENOLATE EQUIVALENTS .2. ASYMMETRIC-SYNTHESIS OF 3-SUBSTITUTED 3-PHENYLPROPIONALDEHYDES VIA METALLATED CHIRAL CINNAMYLAMINES
    AHLBRECHT, H
    ENDERS, D
    SANTOWSKI, L
    ZIMMERMANN, G
    [J]. CHEMISCHE BERICHTE, 1989, 122 (10) : 1995 - 2004
  • [2] Control of the enantiochemistry of electrophilic substitutions of N-pivaloyl-alpha-lithio-o-ethylaniline: Stereoinformation transfer based on the method of organolithium formation
    Basu, A
    Beak, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (06) : 1575 - 1576
  • [3] COMPLEX-INDUCED PROXIMITY EFFECTS - ENANTIOSELECTIVE SYNTHESES BASED ON ASYMMETRIC DEPROTONATIONS OF N-BOC-PYRROLIDINES
    BEAK, P
    KERRICK, ST
    WU, SD
    CHU, JX
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) : 3231 - 3239
  • [4] BEAK P, 1996, ACC CHEM RES, V29
  • [5] GENERATION OF CONFIGURATIONALLY STABLE, ENANTIOENRICHED ALPHA-OXY-ALPHA-METHYLBENZYLLITHIUM - STEREODIVERGENCE OF ITS ELECTROPHILIC SUBSTITUTION
    CARSTENS, A
    HOPPE, D
    [J]. TETRAHEDRON, 1994, 50 (20) : 6097 - 6108
  • [6] ENANTIOSELECTIVE SYNTHESIS VIA SPARTEINE-INDUCED ASYMMETRIC DEPROTONATION
    HOPPE, D
    HINTZE, F
    TEBBEN, P
    PAETOW, M
    AHRENS, H
    SCHWERDTFEGER, J
    SOMMERFELD, P
    HALLER, J
    GUARNIERI, W
    KOLCZEWSKI, S
    HENSE, T
    HOPPE, I
    [J]. PURE AND APPLIED CHEMISTRY, 1994, 66 (07) : 1479 - 1486
  • [7] ASYMMETRIC CARBOLITHIATION OF CINNAMYL DERIVATIVES IN THE PRESENCE OF (-)-SPARTEINE
    KLEIN, S
    MAREK, I
    POISSON, JF
    NORMANT, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (34) : 8853 - 8854
  • [8] OXIDATIVE N-DEARYLATION OF 2-AZETIDINONES - PARA-ANISIDINE AS A SOURCE OF AZETIDINONE NITROGEN
    KRONENTHAL, DR
    HAN, CY
    TAYLOR, MK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (14) : 2765 - 2768
  • [9] ENANTIOSELECTIVE DEPROTONATION AS A VEHICLE FOR THE ASYMMETRIC-SYNTHESIS OF C-2-SYMMETRICAL P-CHIRAL DIPHOSPHINES
    MUCI, AR
    CAMPOS, KR
    EVANS, DA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) : 9075 - 9076
  • [10] (-)-Sparteine-mediated alpha-lithiation of N-Boc-N-(p-methoxyphenyl)benzylamine: Enantioselective syntheses of (S) and (R) mono- and disubstituted N-Boc-benzylamines
    Park, YS
    Boys, ML
    Beak, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (15) : 3757 - 3758