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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