Complementary routes to both enantiomers of pipecolic acid and 4,5-dihydroxypipecolic acid derivatives

被引:24
|
作者
Chattopadhyay, Shital K. [1 ]
Biswas, Titas [1 ]
Biswas, Tanmoy [1 ]
机构
[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India
关键词
imines; allylation; ring-closing metathesis; amino acids;
D O I
10.1016/j.tetlet.2007.12.097
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Complementary new routes to both enantiomers of N-protected pipecolic acid and the corresponding 4,5-dihydroxylated derivatives are developed, which involve stereo-divergent allylation of a chiral N-allylimine and ring-closing metathesis as key steps. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1365 / 1369
页数:5
相关论文
共 50 条
  • [41] Synthesis of new tetrazole-substituted pyroaminoadipic and pipecolic acid derivatives
    Lenda, F
    Guenoun, F
    Tazi, B
    Ben Larbi, N
    Allouchi, H
    Martinez, J
    Lamaty, F
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (02) : 326 - 333
  • [42] Recent advances in asymmetric synthesis of pipecolic acid and derivatives - Review article
    Kadouri-Puchot, C
    Comesse, S
    AMINO ACIDS, 2005, 29 (02) : 101 - 130
  • [43] Mechanism-based inhibition of L-pipecolate oxidase by 4,5-dehydro-L-pipecolic acid
    Zabriskie, TM
    JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (16) : 3046 - 3048
  • [44] Synthesis of pipecolic acid derivatives and related compounds as potential anticonvulsants.
    Ho, B
    Crider, AM
    Cruse, SF
    Hinko, CN
    Andersen, PH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 50 - MEDI
  • [45] Asymmetric synthesis of C-6 substituted pipecolic acid derivatives
    Carbonnel, S
    Fayet, C
    Gelas, J
    Troin, Y
    TETRAHEDRON LETTERS, 2000, 41 (43) : 8293 - 8296
  • [46] Organocatalytic Enantioselective γ-Aminoalkylation of Unsaturated Ester: Access to Pipecolic Acid Derivatives
    Xu, Jianfeng
    Jin, Zhichao
    Chi, Yonggui Robin
    ORGANIC LETTERS, 2013, 15 (19) : 5028 - 5031
  • [47] Synthesis of substituted proline and pipecolic acid derivatives and their use in ACE inhibition
    Beight, DW
    Flynn, GA
    Hofferberth, JE
    Koehl, JR
    Mehdi, S
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 200 - ORGN
  • [48] Synthesis of both enantiomers of lycoperdic acid, an unusual mushroom-derived amino acid
    Katsuta, Ryo
    Ishiuchi, Ryutaro
    Kunisawa, Mikiko
    Yajima, Arata
    Ishigami, Ken
    Nukada, Tomoo
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2021, 85 (01) : 154 - 159
  • [49] DERIVATIVES OF 4,5-DIHYDROXYIMIDAZOLIDINETHIONE-2 - INHIBITORS OF ACID CORROSION.
    Korolenko, V.A.
    Povstyanoi, M.V.
    Eres'ko, V.A.
    Voloshin, V.F.
    Protection of Metals (English translation of Zaschita Metallov), 1982, 18 (05): : 641 - 643
  • [50] PREPARATION OF OPTICALLY ACTIVE PIPECOLIC ACID DERIVATIVES SUITABLE FOR PEPTIDE SYNTHESIS
    BALASPIR.L
    PENKE, B
    PETRES, J
    KOVACS, K
    MONATSHEFTE FUR CHEMIE, 1970, 101 (04): : 1177 - &