An enantioselective synthesis of heteroaromatic N-tosyl α-amino acids

被引:153
作者
Johannsen, M [1 ]
机构
[1] Tech Univ Denmark, Dept Organ Chem, DK-2800 Lyngby, Denmark
关键词
D O I
10.1039/a906758b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new synthesis of optically active beta-indolyl and pyrrolyl N-tosyl alpha-amino acids has been developed which uses readily available starting materials and proceeds with a high degree of enantioselection, giving the alpha-amino acids with up to 96% enantiomeric purity in 89% yield using 1-5 mol% of a chiral copper(I)-Tol-BINAP catalyst.
引用
收藏
页码:2233 / 2234
页数:2
相关论文
共 43 条
  • [1] [Anonymous], 1992, ALDRICHIM ACTA
  • [2] BLASZCZAK LC, 1985, Patent No. 4492694
  • [3] CORDELL GA, 1974, LLOYDIA, V37, P219
  • [4] A novel synthesis of α-amino acid derivatives through catalytic, enantioselective ene reactions of α-imino esters
    Drury, WJ
    Ferraris, D
    Cox, C
    Young, B
    Lectka, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) : 11006 - 11007
  • [5] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS
    DUTHALER, RO
    [J]. TETRAHEDRON, 1994, 50 (06) : 1539 - 1650
  • [6] Erker G., 1990, ANGEW CHEM, V102, P543
  • [7] FANG X, UNPUB
  • [8] Catalytic, enantioselective alkylations of N,O-acetals
    Ferraris, D
    Dudding, T
    Young, B
    Drury, WJ
    Lectka, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) : 2168 - 2169
  • [9] Diastereo- and enantioselective alkylation of α-imino esters with enol silanes catalyzed by (R)-Tol-BINAP-CuClO4•(MeCN)2
    Ferraris, D
    Young, B
    Cox, C
    Drury, WJ
    Dudding, T
    Lectka, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) : 6090 - 6091
  • [10] Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts
    Ferraris, D
    Young, B
    Dudding, T
    Lectka, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) : 4548 - 4549