Substrate selective amide coupling driven by encapsulation of a coupling agent within a self-assembled hexameric capsule

Chem Commun (Camb). 2015 Jan 31;51(9):1658-61. doi: 10.1039/c4cc08833f.

Abstract

Encapsulation of a cationic carbodiimide condensing agent within a self-assembled hexameric capsule made of resorcin[4]arene units provides a nano-environment that efficiently steers the substrate selectivity in the amide synthesis reaction between carboxylic acids and primary amines. While in solution pairs of acids react similarly with a given amine, in the presence of the capsule the formation of the shorter amide is greatly favored.

MeSH terms

  • Amides / chemistry*
  • Calixarenes / chemistry*
  • Capsules*
  • Carbodiimides / chemistry*
  • Models, Molecular
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemistry
  • Substrate Specificity

Substances

  • Amides
  • Capsules
  • Carbodiimides
  • resorcinarene
  • Calixarenes
  • Phenylalanine