Tetrahedron Letters p. 7557 - 7560 (1999)
Update date:2022-09-26
Topics:
Bailey, Patrick D.
Boa, Andrew N.
Baker, S. Richard
Clayson, Joanne
Murray, Ernest J.
Rosair, Georgina M.
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 N4, bis-alkylated at N4 and C6, or tris-alkylated at N4, N1, and C6 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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