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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.

SUBMITTER: Zhang Y

PROVIDER: S-EPMC10321575 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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

Zhang Yuan Y Ourri Benjamin B Skowron Pierre-Thomas PT Jeamet Emeric E Chetot Titouan T Duchamp Christian C Belenguer Ana M AM Vanthuyne Nicolas N Cala Olivier O Dumont Elise E Mandal Pradeep K PK Huc Ivan I Perret Florent F Vial Laurent L Leclaire Julien J

Chemical science 20230524 26

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>i.e.</i>, electrostatic and steric interactions) can transfer this informati ...[more]

PMID: 37416699

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