Clicked H-Shaped Arylopeptoids

Abstract

This study presents a tentative synthesis of supported H-shaped and ladder-type compounds. If the ladders were not accessible, probably due to distance misfits between the reactive centers, a facile method for the synthesis of H-shaped N-alkylated aminomethyl oligobenzamides, i.e., arylopeptoids by on-resin homodimerization via the Copper(I)-Catalyzed-Alkyne-Azide-Cycloaddition (CuAAC) reaction is reported. While successful, a synthetic bottleneck was identified for further oligomer elongation due to congestion when the ligation occurs on solid support. However, this issue was effectively addressed using an elongated oligomer to conduct inter-strand cross-linking. Further CuAAC functionalization could be performed after elongation with additional alkyne groups to enhance diversity.

Keywords

• <i>N</i>-alkylated aromatic oligoamides
• arylopeptoids
• CuAAC
• Copper(I) <i>N</i>-heterocyclic carbene
• solid-phase synthesis
• cross-ligation