Synthesis of optically pure 1,2-diaryl- and 1,2-alkylaryl-1,2-amino sulfides

被引:34
作者
Arroyo, Y
Meana, A
Rodríguez, JF
Santos, M
Sanz-Tejedor, MA
Ruano, JLG
机构
[1] Univ Valladolid, Dept Quim Organ, ETSII, E-47011 Valladolid, Spain
[2] Univ Autonoma Madrid, Dept Quim Organ C1, E-28049 Madrid, Spain
关键词
D O I
10.1021/jo050129x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reactions of the lithium (S)-alpha-(methylthio)-2-(p-toluenesulfinyl)benzyl carbanion with (S)-N-p-tolylsulfinyl aldimines evolve in a completely stereoselective manner providing a one-step synthesis of enantiomerically pure anti-1,2-disubstituted 1,2-amino sulfide derivatives.
引用
收藏
页码:3914 / 3920
页数:7
相关论文
共 57 条
  • [1] Gold complexes with thiosemicarbazones:: reactions of bi- and tridentate thiosemicarbazones with dichloro[2-(dimethylaminomethyl)phenyl-C1,N]gold(III), [Au(damp-C1,N)Cl2]
    Abram, U
    Ortner, K
    Gust, R
    Sommer, K
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (05): : 735 - 744
  • [2] The assembly of oligonuclear nickel(II) complexes from asymmetric compartmental ligands in the presence of alkali metal salts
    Adams, H
    Fenton, DE
    McHugh, PE
    [J]. INORGANIC CHEMISTRY COMMUNICATIONS, 2004, 7 (02) : 147 - 150
  • [3] Oligonuclear nickel(II) complexes of asymmetric compartmental ligands bearing adjacent {N2O} and {N,S,O} donor sets
    Adams, H
    Clunas, S
    Fenton, DE
    Gregson, TJ
    McHugh, PE
    Spey, SE
    [J]. INORGANICA CHIMICA ACTA, 2003, 346 : 239 - 247
  • [4] Copper(II) complexes of unsymmetric compartmental ligands bearing adjacent {N2O}, {N,S,O} donor sets and {N2O}, {N,O} donor sets
    Adams, H
    Clunas, S
    Cummings, LR
    Fenton, DE
    McHugh, PE
    [J]. INORGANIC CHEMISTRY COMMUNICATIONS, 2003, 6 (07) : 837 - 840
  • [5] Cobalt(II) and manganese(II) complexes of unsymmetric compartmental ligands bearing adjacent {N2O} and {N,S,O} donor sets
    Adams, H
    Clunas, S
    Fenton, DE
    Handley, G
    McHugh, PE
    [J]. INORGANIC CHEMISTRY COMMUNICATIONS, 2002, 5 (12) : 1044 - 1047
  • [6] Additions of stabilised and semi-stabilised sulfur ylides to tosyl protected imines: Are they under kinetic or thermodynamic control?
    Aggarwal, VK
    Charmant, JPH
    Ciampi, C
    Hornby, JM
    O'Brien, CJ
    Hynd, G
    Parsons, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (23): : 3159 - 3166
  • [7] Concepts for ligand design in asymmetric catalysis: a study of chiral amino thiol ligands
    Anderson, JC
    Cubbon, R
    Harding, M
    James, DS
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (19) : 3461 - 3490
  • [8] Basu A, 2002, ANGEW CHEM INT EDIT, V41, P717
  • [9] 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
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) : 48 - 49
  • [10] CONCERNING MASS-SPECTRA OF BETA-HETEROSUBSTITUTED THIOETHERS
    CARRENO, MC
    CARRETERO, JC
    RUANO, JLG
    MARTINEZ, MC
    [J]. ORGANIC MASS SPECTROMETRY, 1990, 25 (06): : 339 - 342