Asymmetric Synthesis of Pipecolic Acid and Derivatives

被引:32
|
作者
Cant, Alastair A. [1 ]
Sutherland, Andrew [1 ]
机构
[1] Univ Glasgow, WestCHEM, Sch Chem, Glasgow G12 8QQ, Lanark, Scotland
来源
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 13期
关键词
amino acids; heterocycles; piperidines; asymmetric synthesis; asymmetric catalysis; CYCLIC AMINO-ACIDS; RING-CLOSING METATHESIS; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; INTRAMOLECULAR REACTION; EFFICIENT SYNTHESIS; ENZYMATIC-SYNTHESIS; FORMAL SYNTHESIS; ASPARTIC-ACID;
D O I
10.1055/s-0031-1289767
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The nonproteinogenic alpha-amino acid, L-pipecolic acid and its derivatives are components of a wide range of pharmacologically active compounds. The significant biological activity of these compounds has resulted in the development of many synthetic approaches for their preparation. This review highlights these key methods as well as the application of these compounds for the preparation of enzyme inhibitors, conformationally restricted building blocks and peptidomimetics.
引用
收藏
页码:1935 / 1950
页数:16
相关论文
共 50 条
  • [1] Asymmetric synthesis of unsaturated pipecolic acid derivatives
    Agami, C
    Bihan, D
    Morgentin, R
    PuchotKadouri, C
    [J]. SYNLETT, 1997, (07) : 799 - +
  • [2] Recent advances in asymmetric synthesis of pipecolic acid and derivatives
    C. Kadouri-Puchot
    S. Comesse
    [J]. Amino Acids, 2005, 29 : 101 - 130
  • [3] ASYMMETRIC-SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES
    AGAMI, C
    COUTY, F
    POURSOULIS, M
    VAISSERMANN, J
    [J]. TETRAHEDRON, 1992, 48 (03) : 431 - 442
  • [4] Asymmetric syntheses of pipecolic acid and derivatives
    Couty, F
    [J]. AMINO ACIDS, 1999, 16 (3-4) : 297 - 320
  • [5] Asymmetric syntheses of pipecolic acid and derivatives
    François Couty
    [J]. Amino Acids, 1999, 16 : 297 - 320
  • [6] Recent advances in asymmetric synthesis of pipecolic acid and derivatives - Review article
    Kadouri-Puchot, C
    Comesse, S
    [J]. AMINO ACIDS, 2005, 29 (02) : 101 - 130
  • [7] Asymmetric synthesis of C-6 substituted pipecolic acid derivatives
    Carbonnel, S
    Fayet, C
    Gelas, J
    Troin, Y
    [J]. TETRAHEDRON LETTERS, 2000, 41 (43) : 8293 - 8296
  • [8] An efficient, asymmetric synthesis of pipecolic acid and 2-alkyl pipecolic acids
    Hou, DR
    Hung, SY
    Hu, CC
    [J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (23) : 3858 - 3864
  • [9] Enantioselective synthesis of substituted pipecolic acid derivatives
    Barluenga, J
    Aznar, F
    Valdés, C
    Ribas, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12): : 3918 - 3924
  • [10] Asymmetric syntheses of enantiopure 4-substituted pipecolic acid derivatives
    Agami, C
    Bisaro, F
    Comesse, S
    Guesné, S
    Kadouri-Puchot, C
    Morgentin, R
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (12) : 2385 - 2389