ArticleNature communications2022
Carbene-catalyzed atroposelective synthesis of axially chiral styrenes.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
What it found
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Who cites it
13 citing papers in PubMed, 92 citations in OpenAlex.
- Applying asymmetric-waveform alternating current in nickel-catalyzed asymmetric reductive cross-coupling.Nature communications · 2026Article
- Cooperative NHC and Photoredox Dual Catalysis for the Construction of Carbonyl Compounds.ACS omega · 2026Review
- Palladium-catalyzed redox diversified entry to axially chiral styrenesChemical science · 2025Article
- Cu(I)-catalysed chemo-, regio-, and stereoselective radical 1,2-carboalkynylation with two different terminal alkynes.Nature communications · 2025Article
- Recent advances in organocatalytic atroposelective reactions.Beilstein journal of organic chemistry · 2025Review
- Enantioselective synthesis of saddle-shaped eight-membered lactones with inherent chirality via organocatalytic high-order annulation.Nature communications · 2024Article
- Atroposelective Synthesis of Biaryl N-Oxides via Cu-Catalyzed De Novo Heteroaromatic N-Oxide Ring Formation.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Synthesis of axially chiral diaryl ethersChemical science · 2024Article
- N-Heterocyclic carbene-catalyzed enantioselective synthesis of planar-chiral cyclophanes via dynamic kinetic resolution.Nature communications · 2024Article
- Organocatalytic diastereo- and atroposelective construction of N-N axially chiral pyrroles and indoles.Nature communications · 2024Article
- Discovery and synthesis of atropisomerically chiral acyl-substituted stable vinyl sulfoxonium ylides.Nature chemistry · 2024Article
- Axially chiral styrene-based organocatalysts and their application in asymmetric cascade Michael/cyclization reaction.Chemical science · 2023Article
- High-throughput determination of enantiopurity in atroposelective synthesis of aryl triazoles.Chemical science · 2023Article
Corrections and comments
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Authors and funding
9 authors at 3 institutions in 2 countries.
Funding
Abstract
Axially chiral styrenes bearing a chiral axis between a sterically non-congested acyclic alkene and an aryl ring are difficult to prepare due to low rotational barrier of the axis. Disclosed here is an N-heterocyclic carbene (NHC) catalytic asymmetric solution to this problem. Our reaction involves ynals, sulfinic acids, and phenols as the substrates with an NHC as the catalyst. Key steps involve selective 1,4-addition of sulfinic anion to acetylenic acylazolium intermediate and sequential E-selective protonation to set up the chiral axis. Our reaction affords axially chiral styrenes bearing a chiral axis as the product with up to > 99:1 e.r., > 20:1 E/Z selectivity, and excellent yields. The sulfone and carboxylic ester moieties in our styrene products are common moieties in bioactive molecules and asymmetric catalysis.
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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.