ArticleJournal of the American Chemical Society2020
Single-Step Enantioselective Synthesis of Mechanically Planar Chiral [2]Rotaxanes Using a Chiral Leaving Group Strategy.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 96 citations in OpenAlex.
- A General and Scalable Chiral Surrogate Rotaxane Strategy for Highly Enantioenriched Mechanically Planar Chiral Rotaxanes.Angewandte Chemie (International ed. in English) · 2026Article
- Inverted metal-free active template synthesis of rotaxanes via axle‑mediated macrocyclization.Nature chemistry · 2026Article
- Organocatalytic Enantioselective Divergent Synthesis of Pillar[5]Arenes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Metal-Free Active Template: A Straightforward Route to 4-Aminopyridinium-Based Rotaxane Molecular Shuttles.Angewandte Chemie (International ed. in English) · 2026Article
- Manipulating excited-state dynamics through macrocycle positioning in a rotaxane for sensitive and discriminative methanol sensing.Chemical science · 2026Article
- Spatial Assembly of Mechanically Planar Chiral Rotaxanes on Rationally Designed Cavitands.Angewandte Chemie (International ed. in English) · 2025Article
- Rotaxane synthesisRSC advances · 2025Article
- Crown Ether-Peptide Rotaxanes.Angewandte Chemie (International ed. in English) · 2025Article
- Skeletal Editing of Mechanically Interlocked Molecules: Nitrogen Atom Deletion from Crown Ether-Dibenzylammonium Rotaxanes.Journal of the American Chemical Society · 2024Article
- The End of the Beginning of Mechanical Stereochemistry.Accounts of chemical research · 2024Article
- Photoresponsive Biomimetic Functions by Light-Driven Molecular Motors in Three Dimensionally Printed Liquid Crystal Elastomers.Journal of the American Chemical Society · 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
- Compact Rotaxane Superbases.Journal of the American Chemical Society · 2023Article
- Ring-to-Thread Chirality Transfer in [2]Rotaxanes for the Synthesis of Enantioenriched Lactams.Angewandte Chemie (International ed. in English) · 2022Article
- Mechanically axially chiral catenanes and noncanonical mechanically axially chiral rotaxanes.Nature chemistry · 2022Article
- Transamidation-Driven Molecular Pumps.Journal of the American Chemical Society · 2022Article
- A Co-conformationally "Topologically" Chiral Catenane.Journal of the American Chemical Society · 2022Article
- Phototriggered Complex Motion by Programmable Construction of Light-Driven Molecular Motors in Liquid Crystal Networks.Journal of the American Chemical Society · 2022Article
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Authors and funding
5 authors at 1 institution in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We report a one-step enantioselective synthesis of mechanically planar chiral [2]rotaxanes. Previous studies of such molecules have generally involved the separation of enantiomers from racemic mixtures or the preparation and separation of diastereomeric intermediates followed by post-assembly modification to remove other sources of chirality. Here, we demonstrate a simple asymmetric metal-free active template rotaxane synthesis using a primary amine, an activated ester with a chiral leaving group, and an achiral crown ether lacking rotational symmetry. Mechanically planar chiral rotaxanes are obtained directly in up to 50% enantiomeric excess. The rotaxanes were characterized by NMR spectroscopy, high-resolution mass spectrometry, chiral HPLC, single crystal X-ray diffraction, and circular dichroism. Either rotaxane enantiomer could be prepared selectively by incorporating pseudoenantiomeric cinchona alkaloids into the chiral leaving group.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.