Chiral Nβ-Fmoc-amino alkyl isonitriles in Ugi-4CR: an assembly of novel 1,1′-iminodicarboxylated peptidomimetics

TETRAHEDRON

卷:68

Article

Narendra, N.¹  Vishwanatha, T. M.¹  Nagendra, G.¹  Sureshbabu, Vommina V.¹ 

[1] Bangalore Univ, Dept Studies Chem, Peptide Res Lab, Bangalore 560001, Karnataka, India

关键词: N-beta-Fmoc-amino alkyl isonitriles;    Amino acid esters;    Trifluoroacetic acid;    U-4CR;    U-5C-4CR;    1,1 '-Iminodicarboxylic acid tethered peptidomimetics;   

DOI  :  10.1016/j.tet.2011.12.037

来源: Elsevier

【 摘 要 】

Enantiopure N-beta-Fmoc-amino alkyl isonitriles and amino acid esters have been employed as building blocks in Ugi four-component reaction (U-4CR) to yield 1,1 '-iminodicarboxylated peptidomimetics. By employing trifluoroacetic acid as one of the components, a different outcome has been observed and rationalized. Ugi products are obtained as trifluoroacetamide adducts, which on further reaction under mild acidic conditions lead to the title compounds. The method has also been proven to be useful for the preparation of ethyl, benzyl and tert-butyl esters. (C) 2011 Elsevier Ltd. All rights reserved.

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