In the last decade, many efforts have been devoted to the study of self-assembled supramolecular architectures as nanoreactors for organic reactions. The self-assembled nanoreactors show selective encapsulation of substrates , reaction rate acceleration and the stabilization of reactive species. In addition, many reports show that in the presence of nanoreactors, well known organic reactions proceed with an unconventional regio- and stereochemistry . Self-assembled resorcin[4]arene-based hexameric capsule 1 has been largely exploited as nanoreactor, thanks to its capacity to host selectively the substrates and to its ability to stabilize cationic reactive intermediates . These capsules have been used as nanoreactors for the hydration of aromatic alkynes and terpene cyclization . In this communication, we will show that hexameric resorcinarene capsule is a highly efficient nanoreactor for the proline-catalyzed 1,3-dipolar cycloaddition between nitrones and unsaturated aldehydes with unexpected control on the regio- and stereochemistry of the reaction. The stereochemical outcome of the reaction was also investigated and rationalized by in silico computational studies.
Resorcin[4]arene-Based Hexameric Capsule as Nanoreactor for 1,3-Dipolar Cycloadditions
LA MANNA, PELLEGRINO;TALOTTA, CARMEN;GAETA, CARMINE;SORIENTE, Annunziata;DE ROSA, Margherita;NERI, Placido
2017-01-01
Abstract
In the last decade, many efforts have been devoted to the study of self-assembled supramolecular architectures as nanoreactors for organic reactions. The self-assembled nanoreactors show selective encapsulation of substrates , reaction rate acceleration and the stabilization of reactive species. In addition, many reports show that in the presence of nanoreactors, well known organic reactions proceed with an unconventional regio- and stereochemistry . Self-assembled resorcin[4]arene-based hexameric capsule 1 has been largely exploited as nanoreactor, thanks to its capacity to host selectively the substrates and to its ability to stabilize cationic reactive intermediates . These capsules have been used as nanoreactors for the hydration of aromatic alkynes and terpene cyclization . In this communication, we will show that hexameric resorcinarene capsule is a highly efficient nanoreactor for the proline-catalyzed 1,3-dipolar cycloaddition between nitrones and unsaturated aldehydes with unexpected control on the regio- and stereochemistry of the reaction. The stereochemical outcome of the reaction was also investigated and rationalized by in silico computational studies.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.