Switchable supramolecular helices for asymmetric stereodivergent catalysis

Ran Chen, Ahmad Hammoud, Paméla Aoun, Mayte A. Martínez-Aguirre, Nicolas Vanthuyne, Régina Maruchenko, Patrick Brocorens, Laurent Bouteiller and Matthieu Raynal ()
Additional contact information
Ran Chen: 4 Place Jussieu
Ahmad Hammoud: 4 Place Jussieu
Paméla Aoun: 4 Place Jussieu
Mayte A. Martínez-Aguirre: 4 Place Jussieu
Nicolas Vanthuyne: UMR 7313
Régina Maruchenko: 4 Place Jussieu
Patrick Brocorens: Université de Mons
Laurent Bouteiller: 4 Place Jussieu
Matthieu Raynal: 4 Place Jussieu

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract Despite recent developments on the design of dynamic catalysts, none of them have been exploited for the in-situ control of multiple stereogenic centers in a single molecular scaffold. We report herein that it is possible to obtain in majority any amongst the four possible stereoisomers of an amino alcohol by means of a switchable asymmetric catalyst built on supramolecular helices. Hydrogen-bonded assemblies between a benzene-1,3,5-tricarboxamide (BTA) achiral phosphine ligand coordinated to copper and a chiral BTA comonomer are engaged in a copper-hydride catalyzed hydrosilylation and hydroamination cascade process. The nature of the product stereoisomer is related to the handedness of the helices and can thus be directed in a predictable way by changing the nature of the major enantiomer of the BTA comonomer present in the assemblies. The strategy allows all stereoisomers to be obtained one-pot with similar selectivities by conducting the cascade reaction in a concomitant manner, i.e. without inverting the handedness of the helices, or sequentially, i.e. by switching the handedness of the supramolecular helices between the hydrosilylation and hydroamination steps. Supramolecular helical catalysts appear as a unique and versatile platform to control the configuration of molecules or polymers embedding several stereogenic centers.

Date: 2024
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DOI: 10.1038/s41467-024-48412-z

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