ArticleNature chemistry2016
Catalytic enantioselective addition of organoboron reagents to fluoroketones controlled by electrostatic interactions.
Article in Nature chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed.
- Visible-light-induced trifluoroacetylation reaction of electron-deficient nitrogen heterocycles.Frontiers in chemistry · 2026Article
- Trifluoroethanol-assisted asymmetric propargylic hydrazination to α-tertiary ethynylhydrazines enabled by sterically confined pyridinebisoxazolines.Nature communications · 2025Article
- Electrostatic Interactions in Asymmetric Organocatalysis.Accounts of chemical research · 2023Article
- Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis.Journal of the American Chemical Society · 2023Article
- Chiral α-Stereogenic Oxetanols and AzetidinolsACS catalysis · 2022Article
- ElectrostaticChemical science · 2022Article
- Sustainable radical approaches for cross electrophile coupling to synthesize trifluoromethyl- and allyl-substitutediScience · 2021Article
- Electric Fields in Catalysis: From Enzymes to Molecular Catalysts.ACS catalysis · 2021Article
- Access to enantioenriched compounds bearing challenging tetrasubstituted stereocenters via kinetic resolution of auxiliary adjacent alcohols.Nature communications · 2021Article
- Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality.Chemical reviews · 2021Article
- Regio- and Enantioselective Synthesis of Trifluoromethyl-Substituted Homoallylic α-Tertiary NHAngewandte Chemie (International ed. in English) · 2020Article
- Enantioselective Catalysis of an Anionic Oxy-Cope Rearrangement Enabled by Synergistic Ion Binding.Israel journal of chemistry · 2020Article
- A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing aJournal of the American Chemical Society · 2020Article
- Installation of internal electric fields by non-redox active cations in transition metal complexes.Chemical science · 2019Article
- Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones.Chemical science · 2019Article
- Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.Journal of the American Chemical Society · 2019Article
- Enantioselective Allylation Using Allene, a Petroleum Cracking Byproduct.Journal of the American Chemical Society · 2019Article
- Use of trifluoroacetaldehyde N-tfsylhydrazone as a trifluorodiazoethane surrogate and its synthetic applications.Nature communications · 2019Article
- γ-, Diastereo-, and Enantioselective Addition of MEMO-Substituted Allylboron Compounds to Aldimines Catalyzed by Organoboron-Ammonium Complexes.Angewandte Chemie (International ed. in English) · 2018Article
- Catalytic, Enantioselective Synthesis of Allenyl Boronates.ACS catalysis · 2018Article
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Authors and funding
7 authors.
Funding
Abstract
Organofluorine compounds are central to modern chemistry, and broadly applicable transformations that generate them efficiently and enantioselectively are in much demand. Here we introduce efficient catalytic methods for the addition of allyl and allenyl organoboron reagents to fluorine-substituted ketones. These reactions are facilitated by readily and inexpensively available catalysts and deliver versatile and otherwise difficult-to-access tertiary homoallylic alcohols in up to 98% yield and >99:1 enantiomeric ratio. Utility is highlighted by a concise enantioselective approach to the synthesis of the antiparasitic drug fluralaner (Bravecto, presently sold as the racemate). Different forms of ammonium-organofluorine interactions play a key role in the control of enantioselectivity. The greater understanding of various non-bonding interactions afforded by these studies should facilitate the future development of transformations that involve fluoroorganic entities.
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