ArticleACS central science2016
Synergistic Ion-Binding Catalysis Demonstrated via an Enantioselective, Catalytic [2,3]-Wittig Rearrangement.
Article in ACS central science, 2016. 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, 51 citations in OpenAlex.
- Probing the interactions between cations and borazine analogue complexes.Journal of molecular modeling · 2026Article
- Catalytic Enantioselective Dearomatizing [2,3]-Wittig Rearrangements Allow Divergent [2,3]-, [1,2]-, and Sommelet-Hauser-Type Products.Journal of the American Chemical Society · 2026Article
- The catalytic enantioselective [1,2]-Wittig rearrangement cascade of allylic ethers.Nature chemistry · 2026Article
- Peptidic Catalysts Conformationally Tuned for Fluoride Binding and Delivery.Journal of the American Chemical Society · 2026Article
- Attractive Noncovalent Interactions versus Steric Confinement in Asymmetric Supramolecular Catalysis.Journal of the American Chemical Society · 2026Article
- Recent advances in metal-catalysed asymmetric sigmatropic rearrangements.Chemical science · 2022Review
- ElectrostaticChemical science · 2022Article
- Electric Fields in Catalysis: From Enzymes to Molecular Catalysts.ACS catalysis · 2021Article
- Article
- Enantioselective, Catalytic Multicomponent Synthesis of Homoallylic Amines Enabled by Hydrogen-Bonding and Dispersive Interactions.Journal of the American Chemical Society · 2021Article
- Enantioselective Catalysis of an Anionic Oxy-Cope Rearrangement Enabled by Synergistic Ion Binding.Israel journal of chemistry · 2020Article
- Installation of internal electric fields by non-redox active cations in transition metal complexes.Chemical science · 2019Article
- Chemical composition of DNA-encoded libraries, past present and future.Organic & biomolecular chemistry · 2019Review
- Incorporation of redox-inactive cations promotes iron catalyzed aerobic C-H oxidation at mild potentials.Chemical science · 2018Article
- Catalytic Enantioselective [2,3]-Rearrangements of Allylic Ammonium Ylides: A Mechanistic and Computational Study.Journal of the American Chemical Society · 2017Article
- Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis.Accounts of chemical research · 2017Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Sigmatropic rearrangements number among the most powerful complexity-building transformations in organic synthesis but have remained largely insensitive to enantioselective catalysis due to the diffuse nature of their transition structures. Here, we describe a synergistic ion-binding strategy for asymmetric catalysis of anionic sigmatropic rearrangements. This approach is demonstrated with the enantioselective [2,3]-Wittig rearrangement of α-allyloxy carbonyl compounds to afford highly enantioenriched homoallylic alcohol products. Chiral thiourea catalysts are shown to engage reactive anions and their countercations through a cooperative set of attractive, noncovalent interactions. Catalyst structure-reactivity-selectivity relationship studies and computational analyses provide insight into catalyst-substrate interactions responsible for enantioinduction and allude to the potential generality of this catalytic strategy.
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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.