Asymmetric induction in the nucleophile addition to eta(6)-arene-tricarbonyl-chromium(0) complexes

被引：41
|
作者：
Semmelhack, MF
Schmalz, HG
机构：
[1] Department of Chemistry, Princeton University, Princeton
[2] Institute for Organic Chemistry, Technische Universitat Berlin, D-10623 Berlin
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 18期
关键词：
D O I：
10.1016/0040-4039(96)00572-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The addition of 2-lithio-2-methylpropionitrile (1) to chirally modified eta(6)-arene-tricarbonylchromium complexes (5) leads to the formation of 2-(cyclohex-2-en-1-on-5-yl)-2-methylpropionitrile (4) in good yields and, under thermodynamically controlled conditions, with up to 48% ee. Copyright (C) 1996 Published by Elsevier Science Ltd
引用
收藏
页码：3089 / 3092
页数：4
相关论文
共 50 条
  • [1] ASYMMETRIC OXIDATION OF SULFENYL SUBSTITUTED TRICARBONYL(ETA(6)-ARENE)CHROMIUM(0) COMPLEXES
    GRIFFITHS, SL
    PERRIO, S
    THOMAS, SE
    TETRAHEDRON-ASYMMETRY, 1994, 5 (04) : 545 - 548
  • [2] OXIDATION OF ALKYLTHIO SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES TO ALKYLSULFINYL SUBSTITUTED TRICARBONYL(ETA-6-ARENE)CHROMIUM(0) COMPLEXES
    PEREZENCABO, A
    PERRIO, S
    SLAWIN, AMZ
    THOMAS, SE
    WIERZCHLEYSKI, AT
    WILLIAMS, DJ
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (06): : 629 - 642
  • [3] ALKYLTHIO SUBSTITUTED TRICARBONYL(ETA(6)-ARENE)CHROMIUM(0) COMPLEXES AS SUBSTRATES FOR ASYMMETRIC OXIDATION
    GRIFFITHS, SL
    PERRIO, S
    THOMAS, SE
    TETRAHEDRON-ASYMMETRY, 1994, 5 (09) : 1847 - 1864
  • [4] CATALYTIC ASYMMETRIC INDUCTION .2. CHIRAL TRICARBONYL (ETA-6 ARENE) CHROMIUM (0) COMPLEXES AS ENANTIOSELECTIVE CATALYSTS
    JONES, GB
    HEATON, SB
    TETRAHEDRON-ASYMMETRY, 1993, 4 (02) : 261 - 272
  • [5] Chiral base mediated asymmetric synthesis of tricarbonyl(eta(6)-arene)-chromium complexes
    Ewin, RA
    MacLeod, AM
    Price, DA
    Simpkins, NS
    Watt, AP
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04): : 401 - 415
  • [6] ELECTROPHILIC AROMATIC-SUBSTITUTION IN ARENE-TRICARBONYL-CHROMIUM COMPLEXES
    ROSCA, S
    CHIRALEU, F
    ROSCA, SI
    REVUE ROUMAINE DE CHIMIE, 1991, 36 (4-7) : 693 - 705
  • [7] BASE-CATALYZED HYDROGEN-DEUTERIUM EXCHANGE IN ARENE-TRICARBONYL-CHROMIUM(0) COMPLEXES
    ROSCA, S
    PATRASCU, R
    CHIRALEU, F
    ROSCA, S
    REVUE ROUMAINE DE CHIMIE, 1979, 24 (07) : 1069 - 1076
  • [8] Studies in asymmetric nucleophilic addition to arene chromium tricarbonyl complexes.
    Pearson, AJ
    Paramahamsan, H
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U96 - U96
  • [9] (ETA(6)-ARENE)CHROMIUM TRICARBONYL COMPLEXES AS CHIRAL AUXILIARIES IN ASYMMETRIC DIELS-ALDER REACTIONS
    UEMURA, M
    HAYASHI, Y
    HAYASHI, Y
    TETRAHEDRON-ASYMMETRY, 1993, 4 (11) : 2291 - 2294
  • [10] CHIRAL BASE-MEDIATED ASYMMETRIC-SYNTHESIS OF TRICARBONYL(ETA(6)-ARENE)CHROMIUM COMPLEXES
    PRICE, DA
    SIMPKINS, NS
    MACLEOD, AM
    WATT, AP
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08): : 1961 - 1962
12345