CONFIGURATIONAL STABILITY OF CHIRAL ORGANOLITHIUM COMPOUNDS ON THE TIME-SCALE OF THEIR ADDITION TO ALDEHYDES

被引：0
|
作者：
HOFFMANN, RW [1 ]
JULIUS, M [1 ]
CHEMLA, F [1 ]
RUHLAND, T [1 ]
FRENZEN, G [1 ]
机构：
[1] UNIV MARBURG,FACHBEREICH CHEM,D-35032 MARBURG,GERMANY
来源：
TETRAHEDRON | 1994年 / 50卷 / 20期
关键词：
CONFIGURATIONAL STABILITY; ORGANOLITHIUM COMPOUNDS;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A test based on kinetic resolution has been applied to the alpha-bromo-, alpha-phenylseleno- and alpha-phenylthio-alkyl-lithium compounds 1, which shows that addition of these species to the chiral aldehyde 6 occurs faster than enantiomer equilibration of the organolithium compounds.
引用
收藏
页码：6049 / 6060
页数：12
相关论文
共 40 条
  • [1] What affects the configurational stability of chiral organolithium reagents?
    Reich, H.J.
    Dykstra, R.R.
    Angewandte Chemie (International Edition in English), 1993, 32 (10):
  • [2] Diastereoselective addition of functionalized organolithium compounds to (-)-menthone - synthesis of chiral ligands for enantioselective addition of diethylzinc to aldehydes
    Zagranyarska, I.
    Kostova, K.
    Chimov, A.
    Dimitrov, V.
    BULGARIAN CHEMICAL COMMUNICATIONS, 2017, 49 : 10 - 17
  • [3] CHIRAL ORGANOMETALLIC REAGENTS .5. A TEST ON THE CONFIGURATIONAL STABILITY OF CHIRAL ORGANOLITHIUM COMPOUNDS BASED ON KINETIC RESOLUTION - SCOPE AND LIMITATIONS
    HIRSCH, R
    HOFFMANN, RW
    CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (04): : 975 - 982
  • [4] Functionalized organolithium reagents in the synthesis of chiral ligands for catalytic enantioselective addition of diethylzinc to aldehydes
    Dobrikov, Georgi M.
    Philipova, Irena
    Nikolova, Rositsa
    Shivachev, Boris
    Chimov, Angel
    Dimitrov, Vladimir
    POLYHEDRON, 2012, 45 (01) : 126 - 143
  • [5] ON THE STABILITY OF MULTIPLE TIME-SCALE SYSTEMS
    ABED, EH
    TITS, AL
    INTERNATIONAL JOURNAL OF CONTROL, 1986, 44 (01) : 211 - 218
  • [6] CONFIGURATIONAL STABILITY OF CARBOCATIONS AND ORGANOLITHIUM COMPOUNDS DERIVED FROM HETERO-BRIDGED FERROCENOPHANES
    SOK, KCY
    TAINTURIER, G
    GAUTHERON, B
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 132 (02) : 173 - 189
  • [7] A DFT-derived model predicts solvation-dependent configurational stability of organolithium compounds:: A case study of a chiral α-thioallyllithium compound
    Brandt, P
    Haeffner, F
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) : 48 - 49
  • [8] Catalytic asymmetric addition of aldehydes using organolithium reagents in the presence of commercial available chiral diol ligands
    Zong, Hua
    Huang, Huayin
    Song, Ling
    TETRAHEDRON-ASYMMETRY, 2016, 27 (20-21) : 1069 - 1074
  • [9] 3-aminopyrrolidine lithium amide in enantioselective addition of organolithium compounds onto aromatic aldehydes
    Corruble, A
    Valnot, JY
    Maddaluno, J
    Duhamel, P
    TETRAHEDRON-ASYMMETRY, 1997, 8 (10) : 1519 - 1523
  • [10] 3-Aminopyrrolidine lithium amide in enantioselective addition of organolithium compounds onto aromatic aldehydes
    Corruble, A.
    Valnot, J.-Y.
    Maddaluno, J.
    Duhamel, P.
    Tetrahedron: Asymmetry, 8 (10):
1234