Issue 81, 2019

Spontaneous mirror-symmetry breaking coupled to top-bottom chirality transfer: from porphyrin self-assembly to scalemic Diels–Alder adducts

Abstract

This report shows how the net supramolecular chirality that emerged by spontaneous mirror-symmetry breaking (SMSB) at the mesoscale level can be transferred towards asymmetric solution chemistry. The J-aggregates obtained by self-assembly of an achiral porphyrin act as chiral counteranions in an iminium-promoted Diels–Alder reaction, leading to enantiomeric imbalances in the final adducts.

Graphical abstract: Spontaneous mirror-symmetry breaking coupled to top-bottom chirality transfer: from porphyrin self-assembly to scalemic Diels–Alder adducts

Supplementary files

Article information

Article type
Communication
Submitted
31 Jul 2019
Accepted
16 Sep 2019
First published
25 Sep 2019

Chem. Commun., 2019,55, 12219-12222

Spontaneous mirror-symmetry breaking coupled to top-bottom chirality transfer: from porphyrin self-assembly to scalemic Diels–Alder adducts

A. Arlegui, B. Soler, A. Galindo, O. Arteaga, A. Canillas, J. M. Ribó, Z. El-Hachemi, J. Crusats and A. Moyano, Chem. Commun., 2019, 55, 12219 DOI: 10.1039/C9CC05946F

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