Asymmetric synthesis of β-haloaryl β-amino acid derivatives

被引:18
|
作者
Bull, SD [1 ]
Davies, SG [1 ]
Delgado-Ballester, S [1 ]
Kelly, PM [1 ]
Kotchie, LJ [1 ]
Gianotti, M [1 ]
Laderas, M [1 ]
Smith, AD [1 ]
机构
[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England
关键词
D O I
10.1039/b108573p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lithium N-benzyl-N-alpha -methyl-4-methoxybenzylamide may be employed as a homochiral ammonia equivalent for the synthesis of homochiral beta -haloaryl beta -amino acid derivatives via a strategy involving its conjugate addition to alpha,beta -unsaturated beta -haloaryl acceptors and subsequent oxidative deprotection with ceric ammonium nitrate.
引用
收藏
页码:3112 / 3121
页数:10
相关论文
共 50 条
  • [1] The asymmetric synthesis of β-haloaryl-β-amino acid derivatives
    Bull, SD
    Davies, SG
    Delgado-Ballester, S
    Fenton, G
    Kelly, PM
    Smith, AD
    [J]. SYNLETT, 2000, (09) : 1257 - 1260
  • [2] Asymmetric synthesis of γ-fluorinated α-amino acid derivatives
    Shendage, DM
    Fröhlich, R
    Bergander, K
    Haufe, G
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (04) : 719 - 727
  • [3] Asymmetric amplification in the amino acid-catalyzed synthesis of amino acid derivatives
    Ibrahem, Ismail
    Sunden, Henrik
    Dziedzic, Pawel
    Rios, Ramon
    Cordova, Armando
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) : 1868 - 1872
  • [4] Asymmetric synthesis of β-pyridyl-β-amino acid derivatives
    Bull, SD
    Davies, SG
    Fox, DJ
    Gianotti, M
    Kelly, PM
    Pierres, C
    Savory, ED
    Smith, AD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (16): : 1858 - 1868
  • [5] Catalytic asymmetric synthesis of α- and β-amino phosphonic acid derivatives
    Ma, Jun-An
    [J]. CHEMICAL SOCIETY REVIEWS, 2006, 35 (07) : 630 - 636
  • [6] Asymmetric hydrogenation:: A new method for the synthesis of β-amino acid derivatives
    Hsiao, Y
    Rivera, NR
    Rosner, T
    Krska, SW
    Njolito, E
    Hansen, K
    Wang, F
    Sun, YK
    Armstrong, JD
    Grabowski, EJJ
    Tillyer, RD
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U121 - U121
  • [7] Organocatalytic asymmetric synthesis of β3-amino acid derivatives
    Kim, Sun Min
    Yang, Jung Woon
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (29) : 4737 - 4749
  • [8] A catalytic asymmetric method for the synthesis of γ-unsaturated β-amino acid derivatives
    Lurain, AE
    Walsh, PJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (35) : 10677 - 10683
  • [9] Asymmetric synthesis of quaternary α-amino acid derivatives and their fluorinated analogues
    Santos Fustero
    María Sánchez-Roselló
    Claribel Báez
    Carlos del Pozo
    José L. García Ruano
    José Alemán
    Leyre Marzo
    Alejandro Parra
    [J]. Amino Acids, 2011, 41 : 559 - 573
  • [10] Asymmetric synthesis of quaternary α-amino acid derivatives and their fluorinated analogues
    Fustero, Santos
    Sanchez-Rosello, Maria
    Baez, Claribel
    del Pozo, Carlos
    Garcia Ruano, Jose L.
    Aleman, Jose
    Marzo, Leyre
    Parra, Alejandro
    [J]. AMINO ACIDS, 2011, 41 (03) : 559 - 573