Diamine acylation with amino acid derivatives: an example of proximity effect in organic reactivity induced by supramolecular aggregation

Abstract

Unexpected high yields of diamide 3 are obtained in the reaction of 1,3-propanediamine with an activated ester of l-valine (1) under adverse proportions of the reactants, namely in the presence of an excess of 1,3-propanediamine. It is observed using different conditions that the yield of difunctionalized compound is considerably higher than that expected from a statistical distribution of products. Proximity effects associated to supramolecular interactions explain the described reactivity.