ArticleJournal of the American Chemical Society2014
An in situ directing group strategy for chiral anion phase-transfer fluorination of allylic alcohols.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
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- Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes.Angewandte Chemie (International ed. in English) · 2021Article
- Aluminium-Catalyzed C(sp)-H Borylation of Alkynes.Angewandte Chemie (International ed. in English) · 2021Article
- The Deuterated "Magic Methyl" Group: A Guide to Site-Selective Trideuteromethyl Incorporation and Labeling by Using CDChemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- 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
- Structural Diversity in Supramolecular Organization of Anionic Phosphate Monoesters: Role of Cations.ACS omega · 2019Article
- Enantioselective fluorination of homoallylic alcohols enabled by the tuning of non-covalent interactions.Chemical science · 2018Article
- Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective α-C(spJournal of the American Chemical Society · 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
- Multidimensional Correlations in Asymmetric Catalysis through Parameterization of Uncatalyzed Transition States.Angewandte Chemie (International ed. in English) · 2017Article
- Parametrization of Non-covalent Interactions for Transition State Interrogation Applied to Asymmetric Catalysis.Journal of the American Chemical Society · 2017Article
- Development and Analysis of a Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Acrylates Enabled by Chiral Anion Phase Transfer.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
- Palladium-catalyzed enantioselective 1,1-fluoroarylation of aminoalkenes.Journal of the American Chemical Society · 2015Article
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Authors and funding
3 authors.
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Abstract
An enantioselective fluorination of allylic alcohols under chiral anion phase-transfer conditions is reported. The in situ generation of a directing group proved crucial for achieving effective enantiocontrol. In the presence of such a directing group, a range of acyclic substrates underwent fluorination to afford highly enantioenriched α-fluoro homoallylic alcohols. Mechanistic studies suggest that this transformation proceeds through a concerted enantiodetermining transition state involving both C-F bond formation and C-H bond cleavage.
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