ArticleNature communications2021
Enantioselective preparation of mechanically planar chiral rotaxanes by kinetic resolution strategy.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 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
- Rotaxane synthesisRSC advances · 2025Article
- Measuring the stereogenic remoteness in non-central chirality: a stereocontrol connectivity index for asymmetric reactions.Beilstein journal of organic chemistry · 2025Article
- The End of the Beginning of Mechanical Stereochemistry.Accounts of chemical research · 2024Article
- Facial Selectivity in Mechanical Bond Formation: Axially Chiral Enantiomers and Geometric Isomers from a Simple Prochiral Macrocycle.Journal of the American Chemical Society · 2024Article
- The Final Stereogenic Unit of [2]Rotaxanes: Type 2 Geometric Isomers.Journal of the American Chemical Society · 2024Article
- Mechanically Planar-to-Point Chirality Transmission in [2]Rotaxanes.Journal of the American Chemical Society · 2024Article
- Strategies for chiral separation: from racemate to enantiomer.Chemical science · 2023Review
- Mechanically axially chiral catenanes and noncanonical mechanically axially chiral rotaxanes.Nature chemistry · 2022Article
- A Co-conformationally "Topologically" Chiral Catenane.Journal of the American Chemical Society · 2022Article
- Rotaxanes with dynamic mechanical chirality: Systematic studies on synthesis, enantiomer separation, racemization, and chiral-prochiral interconversion.Frontiers in chemistry · 2022Article
- Direct synthetic routes to functionalised crown ethers.Organic chemistry frontiers : an international journal of organic chemistry · 2021Review
- Mechanically Interlocked Chiral Self-Templated [2]Catenanes from 2,6-Bis(1,2,3-triazol-4-yl)pyridine (btp) Ligands.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Diastereoselective Amplification of a Mechanically Chiral [2]Catenane.Journal of the American Chemical Society · 2021Article
- Spin-labelled mechanically interlocked molecules as models for the interpretation of biradical EPR spectra.Chemical science · 2021Article
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Authors and funding
7 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Asymmetric synthesis of mechanically planar chiral rotaxanes and topologically chiral catenanes has been a long-standing challenge in organic synthesis. Recently, an excellent strategy was developed based on diastereomeric synthesis of rotaxanes and catenanes with mechanical chirality followed by removal of the chiral auxiliary. On the other hand, its enantioselective approach has been quite limited. Here, we report enantioselective preparation of mechanically planar chiral rotaxanes by kinetic resolution of the racemates via remote asymmetric acylation of a hydroxy group in the axis component, which provides an unreacted enantiomer in up to >99.9% ee in 29% yield (the theoretical maximum yield of kinetic resolution of racemate is 50%). While the rotaxane molecules are expected to have conformational complexity, our original catalysts enabled to discriminate the mechanical chirality of the rotaxanes efficiently with the selectivity factors in up to 16.
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