ArticleJournal of the American Chemical Society2018
Central-to-Helical-to-Axial-to-Central Transfer of Chirality with a Photoresponsive Catalyst.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed.
- Enantioselective construction of polychiral helical compounds via dynamic kinetic resolution.Nature communications · 2026Article
- General strategy for boosting the performance of speed-tunable rotary molecular motors with visible light.Science advances · 2025Article
- Coupling Rotary Motion to Helicene Inversion within a Molecular Motor.Angewandte Chemie (International ed. in English) · 2025Article
- A Multiresponsive Ferrocene-Based Chiral Overcrowded Alkene Twisting Liquid Crystals.Angewandte Chemie (International ed. in English) · 2025Article
- Switchable supramolecular helices for asymmetric stereodivergent catalysis.Nature communications · 2024Article
- Padlocking dihydrofurannulation for the control of small degree of helicity built on a fused-tetracyclic core.Chemical science · 2024Article
- Molecular Motors' Magic Methyl and Its Pivotal Influence on Rotation.Journal of the American Chemical Society · 2024Article
- Enlightening dynamic functions in molecular systems by intrinsically chiral light-driven molecular motors.Chemical Society reviews · 2023Review
- Accounts of applied molecular rotors and rotary motors: recent advances.Nanoscale advances · 2023Review
- Designing P-type bi-stable overcrowded alkene-based chiroptical photoswitches.Chemical science · 2023Article
- Dirigent gene editing of gossypol enantiomers for toxicity-depleted cotton seeds.Nature plants · 2023Article
- Enantioselective Synthesis of Atropisomers by Oxidative Aromatization with Central-to-Axial Conversion of Chirality.Molecules (Basel, Switzerland) · 2023Review
- Enantiodivergent epoxidation of alkenes with a photoswitchable phosphate manganese-salen complex.Nature synthesis · 2022Article
- Photogearing as a concept for translation of precise motions at the nanoscale.Nature chemistry · 2022Article
- Rational design of allosteric switchable catalysts.Exploration (Beijing, China) · 2022Review
- Directing Coupled Motion with Light: A Key Step Toward Machine-Like Function.Chemical reviews · 2021Article
- Steric Effects on the Thermal Processes of Hemithioindigo Based Molecular Motor Rotation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Competition between cyclization and unusual Norrish type I and type II nitro-acyl migration pathways in the photouncaging of 1-acyl-7-nitroindoline revealed by computations.Scientific reports · 2021Article
- Molecular motor-functionalized porphyrin macrocycles.Nature communications · 2020Article
- A molecular assembler that produces polymers.Nature communications · 2020Article
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Recent advances in molecular design have displayed striking examples of dynamic chirality transfer between various elements of chirality, e.g., from central to either helical or axial chirality and vice versa. While considerable progress in atroposelective synthesis has been made, it is intriguing to design chiral molecular switches able to provide selective and dynamic control of axial chirality with an external stimulus to modulate stereochemical functions. Here, we report the synthesis and characterization of a photoresponsive bis(2-phenol)-substituted molecular switch 1. The unique design exhibits a dynamic hybrid central-helical-axial transfer of chirality. The change of preferential axial chirality in the biaryl motif is coupled to the reversible switching of helicity of the overcrowded alkene core, dictated by the fixed stereogenic center. The potential for dynamic control of axial chirality was demonstrated by using ( R)-1 as switchable catalyst to direct the stereochemical outcome of the catalytic enantioselective addition of diethylzinc to aromatic aldehydes, with successful reversal of enantioselectivity for several substrates.
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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.