ArticleJournal of the American Chemical Society2014
Asymmetric fluorination of α-branched cyclohexanones enabled by a combination of chiral anion phase-transfer catalysis and enamine catalysis using protected amino acids.
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 38 papers.
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Who cites it
38 citing papers in PubMed.
- Counteranion-mediated dynamic kinetic asymmetric fluorination to access sulfur-stereogenic center.Nature communications · 2026Article
- Asymmetric phase-transfer catalysis.Nature reviews. Chemistry · 2024Review
- Multifunctional Organocatalysts - Singly-Linked and Macrocyclic Bisphosphoric Acids for Asymmetric Phase-Transfer and Brønsted-Acid Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Article
- Synergistic Strategies in Aminocatalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Catalytic alkene skeletal modification for the construction of fluorinated tertiary stereocenters.Chemical science · 2022Article
- New anionic cobalt(III) complexes enable enantioselective synthesis of spiro-fused oxazoline and iodoacetal derivatives.Frontiers in chemistry · 2022Article
- Enantio- and Diastereoselective, Complete Hydrogenation of Benzofurans by Cascade Catalysis.Angewandte Chemie (International ed. in English) · 2021Article
- Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization.Journal of the American Chemical Society · 2020Article
- Catalytic Dynamic Kinetic Resolutions in Tandem to Construct Two-Axis Terphenyl Atropisomers.Journal of the American Chemical Society · 2020Article
- Hydrogen Bonding Phase-Transfer Catalysis with Ionic Reactants: Enantioselective Synthesis of γ-Fluoroamines.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
- Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.Angewandte Chemie (International ed. in English) · 2019Article
- Application of theMolecules (Basel, Switzerland) · 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
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Funding
Abstract
We report a study involving the successful merger of two separate chiral catalytic cycles: a chiral anion phase-transfer catalysis cycle to activate Selectfluor and an enamine activation cycle, using a protected amino acid as organocatalyst. We have demonstrated the viability of this approach with the direct asymmetric fluorination of α-substituted cyclohexanones to generate quaternary fluorine-containing stereocenters. With these two chiral catalytic cycles operating together in a matched sense, high enantioselectivites can be achieved, and we envisage that this dual catalysis method has the potential to be more broadly applicable, given the breadth of enamine catalysis. It also represents a rare example of chiral enamine catalysis operating successfully on α-branched ketones, substrates commonly inert to this activation mode.
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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.