Issue 26, 2023

Self-assembly of achiral building blocks into chiral cyclophanes using non-directional interactions

Abstract

The diastereoselective assembly of achiral constituents through a single spontaneous process into complex covalent architectures bearing multiple stereogenic elements still remains a challenge for synthetic chemists. Here, we show that such an extreme level of control can be achieved by implementing stereo-electronic information on synthetic organic building blocks and templates and that non-directional interactions (i.e., electrostatic and steric interactions) can transfer this information to deliver, after self-assembly, high-molecular weight macrocyclic species carrying up to 16 stereogenic elements. Beyond the field of supramolecular chemistry, this proof of concept should stimulate the on-demand production of highly structured polyfunctional architectures.

Graphical abstract: Self-assembly of achiral building blocks into chiral cyclophanes using non-directional interactions

Supplementary files

Article information

Article type
Edge Article
Submitted
07 mar 2023
Accepted
23 mai 2023
First published
24 mai 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 7126-7135

Self-assembly of achiral building blocks into chiral cyclophanes using non-directional interactions

Y. Zhang, B. Ourri, P. Skowron, E. Jeamet, T. Chetot, C. Duchamp, A. M. Belenguer, N. Vanthuyne, O. Cala, E. Dumont, P. K. Mandal, I. Huc, F. Perret, L. Vial and J. Leclaire, Chem. Sci., 2023, 14, 7126 DOI: 10.1039/D3SC01235B

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