2-DIBENZYLAMINOBUTANE-1,4-DIOL - AN EFFECTIVE CHIRAL BUILDING-BLOCK FOR THE SYNTHESIS OF 1,2-AMINO ALCOHOLS

被引:0
|
作者
GMEINER, P
KARTNER, A
机构
来源
SYNTHESIS-STUTTGART | 1995年 / 01期
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Regioselective activation and protection of the chiral building block 1, readily available from L-aspartic acid, leads to the key intermediate 8. Employing classical nucleophiles, heterocyclic anions or organocuprates, 8 could be transformed into the displacement products 9. Finally, hydrolysis affords the homochiral 1,2-amino alcohols 4 in 48-77% yield (based on 8).
引用
收藏
页码:83 / 86
页数:4
相关论文
共 50 条
  • [31] PREPARATION OF ACTIVATED IMINES AND THEIR CONDENSATION WITH ALLYLSTANNANES - STEREOSELECTIVE SYNTHESIS OF 1,2-AMINO ALCOHOLS
    CIUFOLINI, MA
    SPENCER, GO
    JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (20): : 4739 - 4741
  • [32] Stereoselective synthesis of 1,2-amino alcohols by asymmetric borane reduction of α-oxoketoxime ethers
    Masui, M
    Shioiri, T
    TETRAHEDRON LETTERS, 1998, 39 (29) : 5195 - 5198
  • [33] 2,5-Diformylbenzene-1,4-diol: A versatile building block for the synthesis of ditopic redox-active Schiff base ligands
    Kretz, Tonia
    Bats, Jan Willem
    Lerner, Hans-Wolfram
    Wagner, Matthias
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2007, 62 (01): : 66 - 74
  • [34] One-pot synthesis of trisubstituted 1,2-amino alcohols from deprotonated α-amino nitriles
    Kison, Coralie
    Opatz, Till
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (16) : 2740 - 2745
  • [35] ORGN 982-The synthesis of novel chiral 1,2-amino alcohols and their use in directing the addition of diethylzinc to aromatic aldehydes
    Binder, Caitlin M.
    Singaram, Bakthan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [36] LIPASE-CATALYZED RESOLUTION OF CHIRAL 2-AMINO 1-ALCOHOLS
    FRANCALANCI, F
    CESTI, P
    CABRI, W
    BIANCHI, D
    MARTINENGO, T
    FOA, M
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (23): : 5079 - 5085
  • [37] Asymmetric self-replication of chiral 1,2-amino alcohols by highly enantioselective autoinductive reduction
    Shibata, T
    Takahashi, T
    Konishi, T
    Soai, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (22): : 2458 - 2460
  • [38] 2-IMIDAZOLIDINONES FROM 1,2-AMINO ALCOHOLS - APPLICATION TO THE SYNTHESIS OF A 2-IMIDAZOLIDINONE ANALOG OF PILOCARPINE
    KIM, TH
    RAPOPORT, H
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11): : 3699 - 3702
  • [39] Synthesis and structural analysis of sterically hindered chiral 1,4-diol ligands derived from the lignan hydroxymatairesinol
    Brusentsev, Yury
    Sandberg, Thomas
    Hotokka, Matti
    Sjoholm, Rainer
    Eklund, Patrik
    TETRAHEDRON LETTERS, 2013, 54 (09) : 1112 - 1115
  • [40] Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids
    Hall, Christopher J. J.
    Goundry, William R. F.
    Donohoe, Timothy J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (13) : 6981 - 6985