ArticleJournal of the American Chemical Society2024
Mechanically Planar-to-Point Chirality Transmission in [2]Rotaxanes.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- A General and Scalable Chiral Surrogate Rotaxane Strategy for Highly Enantioenriched Mechanically Planar Chiral Rotaxanes.Angewandte Chemie (International ed. in English) · 2026Article
- Spatial Assembly of Mechanically Planar Chiral Rotaxanes on Rationally Designed Cavitands.Angewandte Chemie (International ed. in English) · 2025Article
- Cooperative reversible assembly in triply interlocked AlChemical science · 2025Article
- A Thiourea-Based Rotaxane Catalyst: Nucleophilic Fluorination Phase-Transfer Process Unlocked by the Mechanical Bond.Organic letters · 2025Article
- Mechanical interlocking of metal organic cages.Communications chemistry · 2025Review
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Herein we describe an effective transmission of chirality, from mechanically planar chirality to point chirality, in hydrogen-bonded [2]rotaxanes. A highly selective mono-N-methylation of one (out of four) amide N atom at the macrocyclic counterpart of starting achiral rotaxanes generates mechanically planar chirality. Followed by chiral resolution, both enantiomers were subjected to a base-promoted intramolecular cyclization, where their interlocked threads were transformed into new lactam moieties. As a matter of fact, the mechanically planar chiral information was effectively transferred to the resulting stereocenters (covalent chirality) of the newly formed heterocycles. Upon removing the entwined macrocycle, the final lactams were obtained with high enantiopurity.
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Registered trials
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