Solid-Phase Synthesis of Oligo(p-benzamide) Foldamers

Significance

The first solid-phase synthesis of oligo(p-benzamide)s (OPBAs) up to the decamer 5 via acylation of secondary aromatic amines 3 on a Wang resin was described. Thus, the attachment of Fmoc- and PMB-protected p-amino benzoic acid chloride 1 (derived from 2) with Wang resin (1.2 mmol OH g^-1) followed by Fmoc deprotection with piperidine in DMF gave the secondary aromatic amine immobilized on resin 3a (n = 1). The sequence was repeated nine times to prepare a deca(p-benzamide) 3j (n = 10), which was treated with TFA to release the decamer 5.