Three-component synthesis of highly functionalized aziridines containing a peptide side chain and their one-step transformation into β-functionalized α-ketoamides

• Lena Huck,
• Juan F. González,
• Elena de la Cuesta and
• J. Carlos Menéndez

Beilstein J. Org. Chem. 2016, 12, 1772–1777, doi:10.3762/bjoc.12.166

• . Their transformation into β-trifluoroacetamido-α-ketoamide and α,β-diketoamide frameworks was also achieved in a single step. Keywords: α-ketoamides; aziridines; multicomponent reactions; nitrogen heterocycles; one-pot reactions; peptide mimics; vicinal tricarbonyl compounds; Introduction Aziridine

• transformed into the observed product 6 by intramolecular transfer of the trifluoroacetyl group. Finally, bearing in mind the interest of 1,2,3-tricarbonyl compounds (vicinal tricarbonyl compounds, VCTs) both as structural fragments of protease inhibitors [31] and synthetic intermediates [32][33], we also

• . Transformation of aziridines 2 into vicinal tricarbonyl compounds 11 and transformation of the latter into nitrogen heterocycles 12 and 13, containing a peptide side chain. Mechanistic proposal for the transformation of aziridines 2 into compounds 11. Results obtained in the aziridine synthesis. Results of the