ArticleAngewandte Chemie (International ed. in English)2020
Bidentate Chiral Bis(imidazolium)-Based Halogen-Bond Donors: Synthesis and Applications in Enantioselective Recognition and Catalysis.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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25 citing papers in PubMed, 112 citations in OpenAlex.
- Neutral chiral bidentate tellurium-triazoles for enantioselective non-covalent chalcogen-bonding catalysis.Nature communications · 2026Article
- Highly Enantioselective Organocatalysis with Bidentate Halogen Bond Donors.Angewandte Chemie (International ed. in English) · 2025Article
- Asymmetric Counteranion-Directed Halogen Bonding Catalysis.Journal of the American Chemical Society · 2025Article
- Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt.Beilstein journal of organic chemistry · 2025Article
- Pnictogen bonding in imide derivatives for chiral folding and self-assembly.Chemical science · 2024Article
- Counteranion-mediated efficient iodine capture in a hexacationic imidazolium organic cage enabled by multiple non-covalent interactions.Nature communications · 2023Article
- Enantioselective dearomatization reactions of heteroarenes by anion-binding organocatalysis.Chemical communications (Cambridge, England) · 2023Review
- Recent Developments and Trends in Asymmetric Organocatalysis.European journal of organic chemistry · 2023Review
- Chiral Bromonium Salt (Hypervalent Bromine(III)) withMolecules (Basel, Switzerland) · 2023Article
- Stereochemistry Controls Dihydrogen Bonding Strengths in Chiral Amine Boranes Adducts.Angewandte Chemie (International ed. in English) · 2022Article
- Selective Potassium Chloride Recognition, Sensing, Extraction, and Transport Using a Chalcogen-Bonding Heteroditopic Receptor.Journal of the American Chemical Society · 2022Article
- Stereoselective Processes Based on σ-Hole Interactions.Molecules (Basel, Switzerland) · 2022Review
- Halogen bonding organocatalysis enhanced through intramolecular hydrogen bonds.Chemical communications (Cambridge, England) · 2022Article
- Evaluation of Halogenopyridinium Cations as Halogen Bond Donors.Crystal growth & design · 2021Article
- Modulating Chalcogen Bonding and Halogen Bonding Sigma-Hole Donor Atom Potency and Selectivity for Halide Anion Recognition.Angewandte Chemie (International ed. in English) · 2021Article
- Enantioselective Michael addition to vinyl phosphonatesChemical science · 2021Article
- Neutral Chiral Tetrakis-Iodo-Triazole Halogen-Bond Donor for Chiral Recognition and Enantioselective Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Halides as versatile anions in asymmetric anion-binding organocatalysis.Beilstein journal of organic chemistry · 2021Review
- Facile and Reliable Emission-Based Nanomolar Anion Sensing by Luminescent Iridium Receptors Featuring Chelating Halogen-Bonding Sites.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Design and Synthesis of a Chiral Halogen-Bond Donor with a SpMolecules (Basel, Switzerland) · 2020Article
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4 authors at 1 institution in 1 country.
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Abstract
Even though halogen bonding-the noncovalent interaction between electrophilic halogen substituents and Lewis bases-has now been established in molecular recognition and catalysis, its use in enantioselective processes is still very rarely explored. Herein, we present the synthesis of chiral bidentate halogen-bond donors based on two iodoimidazolium units with rigidly attached chiral sidearms. With these Lewis acids, chiral recognition of a racemic diamine is achieved in NMR studies. DFT calculations support a 1:1 interaction of the halogen-bond donor with both enantiomers and indicate that the chiral recognition is based on a different spatial orientation of the Lewis bases in the halogen-bonded complexes. In addition, moderate enantioselectivity is achieved in a Mukaiyama aldol reaction with a preorganized variant of the chiral halogen-bond donor. This represents the first case in which asymmetric induction was realized with a pure halogen-bond donor lacking any additional active functional groups.
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