Issue 9, 2015

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
05 Nov 2014
Accepted
05 Dec 2014
First published
08 Dec 2014

Chem. Commun., 2015,51, 1658-1661

Author version available

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

S. Giust, G. La Sorella, L. Sperni, G. Strukul and A. Scarso, Chem. Commun., 2015, 51, 1658 DOI: 10.1039/C4CC08833F

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