Chiral imines 1a,b, already synthesized in our laboratory, were converted in good yield by reduction into the corresponding N-benzyl-gamma-lactams 2a,b. Desilylation followed by oxidation of the hydroxymethyl functionality gave the N-benzyl-beta-amino acids 7a,b in good yield and high purity. Starting from compound 7a, the corresponding beta-peptoid dimer 8 was prepared, together with its derivatives 9 and 10, this latter displaying conformational restriction about the peptide bond, as evidenced by 1H NMR data.

Beta-Peptoids: synthesis of a novel dimer having a fully extended conformation

MARTELLI, GIANLUCA;RINALDI, SAMUELE;CASTELLUCCI, NICOLA;TOMASINI, CLAUDIA
2012

Abstract

Chiral imines 1a,b, already synthesized in our laboratory, were converted in good yield by reduction into the corresponding N-benzyl-gamma-lactams 2a,b. Desilylation followed by oxidation of the hydroxymethyl functionality gave the N-benzyl-beta-amino acids 7a,b in good yield and high purity. Starting from compound 7a, the corresponding beta-peptoid dimer 8 was prepared, together with its derivatives 9 and 10, this latter displaying conformational restriction about the peptide bond, as evidenced by 1H NMR data.
G. Martelli; A. Monsignori; M. Orena; S. Rinaldi; N. Castellucci; C. Tomasini
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/121556
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