Diamine acylation with amino acid derivatives: an example of proximity effect in organic reactivity induced by supramolecular aggregation. Issue 9 (25th February 2015)

• Record Type: Journal Article
• Authors: Felip-León, Carles; Segarra-Maset, María D.; Escuder, Beatriu; Miravet, Juan F.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 9(2015)
• Page Start: 1132
• Page End: 1134
• Publication Date: 2015-02-25
• Subjects: OAPNWOBUQCNJBS-DQEYMECFSA-N -- QOWBDAUCIVQWKX-AWEZNQCLSA-N; Proximity effects -- Supramolecular catalysis -- Chemoselectivity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.01.094
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Unexpected high yields of diamide3 are obtained in the reaction of 1, 3-propanediamine with an activated ester ofl -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.