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Piperazine-2,3,5-triones in the synthesis of constrained peptides

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
40
Issue
42
Identifiers
DOI: 10.1016/s0040-4039(99)01602-0
Keywords
  • Amino Acids And Derivatives
  • Peptide Analogues/Mimetics
  • Piperazines/Piperazinones

Abstract

Abstract Amino acid amides react with diethyl oxalate and sodium ethoxide to yield 6-substituted piperazine-2,3,5-triones, which can be mono-alkylated at N 4, bis-alkylated at N 4 and C 6, or tris-alkylated at N 4, N 1, and C 6 under mild basic conditions; this provides access to i) α,α-disubstituted cyclic peptide derivatives; ii) constrained peptides via C(α)N bond formation; iii) DKP analogues.

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