ArticleProceedings of the National Academy of Sciences of the United States of America2013
A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed.
- Multifunctional Organocatalysts - Singly-Linked and Macrocyclic Bisphosphoric Acids for Asymmetric Phase-Transfer and Brønsted-Acid Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
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- Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters.Chemical science · 2022Article
- A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis.Journal of the American Chemical Society · 2021Article
- Catalytic Dynamic Kinetic Resolutions in Tandem to Construct Two-Axis Terphenyl Atropisomers.Journal of the American Chemical Society · 2020Article
- Regio- and Enantioselective Bromocyclization of Difluoroalkenes as a Strategy to Access Tetrasubstituted Difluoromethylene-Containing Stereocenters.Journal of the American Chemical Society · 2020Article
- Enantioselective Kinetic Resolution/Desymmetrization ofAdvanced synthesis & catalysis · 2020Article
- Enantioselective construction of remote tertiary carbon-fluorine bonds.Nature chemistry · 2019Article
- Enantioselective fluorination of homoallylic alcohols enabled by the tuning of non-covalent interactions.Chemical science · 2018Article
- Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs.Chemical reviews · 2018Review
- Streamlined asymmetric α-difunctionalization of ynones.Nature communications · 2018Article
- Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis.Accounts of chemical research · 2017Article
- Enantioselective Synthesis of β-Fluoro Amines via β-Amino α-Fluoro Nitroalkanes and a Traceless Activating Group Strategy.Journal of the American Chemical Society · 2016Article
- Biomimetic Approach to the Catalytic Enantioselective Synthesis of Flavonoids.Journal of the American Chemical Society · 2016Article
- Enantiodivergent Fluorination of Allylic Alcohols: Data Set Design Reveals Structural Interplay between Achiral Directing Group and Chiral Anion.Journal of the American Chemical Society · 2016Article
- Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetalsChemical science · 2016Article
- Catalytic Asymmetric Mannich Reactions with Fluorinated Aromatic Ketones: Efficient Access to Chiral β-Fluoroamines.Angewandte Chemie (International ed. in English) · 2016Article
- Palladium-catalyzed enantioselective 1,1-fluoroarylation of aminoalkenes.Journal of the American Chemical Society · 2015Article
- Enantioselective small molecule synthesis by carbon dioxide fixation using a dual Brønsted acid/base organocatalyst.Journal of the American Chemical Society · 2015Article
- Enantioselective and diastereoselective azo-coupling/iminium-cyclizations: a unified strategy for the total syntheses of (-)-psychotriasine and (+)-pestalazine B.Chemical science · 2015Article
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6 authors.
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Abstract
We report a catalytic enantioselective electrophilic fluorination of alkenes to form tertiary and quaternary C(sp3)-F bonds and generate β-amino- and β-aryl-allylic fluorides. The reaction takes advantage of the ability of chiral phosphate anions to serve as solid-liquid phase transfer catalysts and hydrogen bond with directing groups on the substrate. A variety of heterocyclic, carbocyclic, and acyclic alkenes react with good to excellent yields and high enantioselectivities. Further, we demonstrate a one-pot, tandem dihalogenation-cyclization reaction, using the same catalytic system twice in series, with an analogous electrophilic brominating reagent in the second step.
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