Abstract
Chiral imines 1a,b, already synthesized in our laboratory, were converted in good yield by reduction into the corresponding N-benzyl-γ-lactams 2a,b. Desilylation followed by oxidation of the hydroxymethyl functionality gave the N-benzyl-β-amino acids 5a,b in good yield and high purity. Starting from compound 6a, the corresponding β-peptoid dimer 8 was prepared, together with its derivatives 9 and 10, these latter displaying conformational restriction about the peptide bond, as evidenced by NMR data.
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We thank Polytechnic University of Marche for financial support.
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Martelli, G., Monsignori, A., Orena, M. et al. β-Peptoids: synthesis of a novel dimer having a fully extended conformation. Amino Acids 43, 2005–2014 (2012). https://doi.org/10.1007/s00726-012-1275-1
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DOI: https://doi.org/10.1007/s00726-012-1275-1