Organic Chemistry

Encoding stereochemical molecular information on cyclophanes using non-directional interactions and achiral building blocks

Authors

Abstract

The stereoselective assembly of achiral constituents through a single spontaneous process into complex covalent architectures bearing multiple stereogenic elements currently seems out of reach to the synthetic chemist. It even seems beyond what nature itself has managed to attain through evolution. Here, we show that such an extreme level of control can be achieved by molecular programming, i.e. by implementing stereo-electronic information on synthetic organic building blocks and exploiting the features of the covalent reactions and interactions, whose interplay acts as a powerful assembling algorithm. Remarkably, we show that non-directional bonds and interactions can reliably transfer this information, delivering in near to physiological conditions, high-molecular weight macrocyclic species carrying up to 8-bits of conformational and configuration information. Beyond the field of supramolecular chemistry, this proof of concept should stimulate the on-demand production of highly structured polyfunctional architectures.

Content

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Supplementary material

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Supporting Information
"Crystallographic data for the structures reported in this Article have been deposited at the Cambridge Crystallographic Data Centre, under deposition numbers CCDC 1554744, 2003290, 2001333, 2003509 for A4-a, A4-a-Cadav, A4-a-Put and B8 respectively. Copies of the data can be obtained free of charge via https://www.ccdc.cam.ac.uk/structures/. All other data supporting the findings of this study, including synthetic and analytical procedures are available within the Article and its Supplementary Information, or from the corresponding author upon reasonable request."