Spontaneous Mirror-symmetry Breaking Coupled to Top-bottom Chirality Transfer: from Porphyrin Self-assembly to Scalemic Diels-Alder Adducts

Overview

Journal Chem Commun (Camb)

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2019 Sep 26

PMID 31553004

Citations 8

Authors

Aitor Arlegui

Bernat Soler

Alex Galindo

Oriol Arteaga

Adolf Canillas

Josep M Ribo

Zoubir El-Hachemi

Joaquim Crusats

Albert Moyano

Affiliations

Soon will be listed here.

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.

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