ArticleOrganic letters2018
Disulfide-Bridged Peptides That Mediate Enantioselective Cycloadditions through Thiyl Radical Catalysis.
Article in Organic letters, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Clarifying Stereochemical Outcomes in Radical-Initiated Vinyl Cyclopropane Cycloadditions within the Beckwith-Houk Framework.Organic chemistry frontiers : an international journal of organic chemistry · 2026Article
- Peptidyl Glycosyl Thiols and Disulfides for Enantioselective Hydrogen Atom Transfer (HAT) and Thiyl Radical Catalysis.The Journal of organic chemistry · 2025Article
- Hierarchically Porous Poly(aryl thioether)s Through Dynamic Linker Engineering for Thiyl Radical Photocatalysis.Small (Weinheim an der Bergstrasse, Germany) · 2025Article
- Enantioselective radical chemistry: a bright future ahead.Beilstein journal of organic chemistry · 2025Article
- Enantioselective radical cascade cyclization via Ti-catalyzed redox relay.Tetrahedron letters · 2023Article
- Formal Cycloadditions Driven by the Homolytic Opening of Strained, Saturated Ring Systems.Angewandte Chemie (International ed. in English) · 2023Review
- Strain-Release [2π + 2σ] Cycloadditions for the Synthesis of Bicyclo[2.1.1]hexanes Initiated by Energy Transfer.Journal of the American Chemical Society · 2022Article
- Kinetic Analysis of a Cysteine-Derived Thiyl-Catalyzed Asymmetric Vinylcyclopropane Cycloaddition Reflects Numerous Attractive Noncovalent Interactions.Journal of the American Chemical Society · 2021Article
- Controlling Enantioselectivity and Diastereoselectivity in Radical Cascade Cyclization for Construction of Bicyclic Structures.Journal of the American Chemical Society · 2021Article
- Catalytic asymmetric and stereodivergent oligonucleotide synthesis.Science (New York, N.Y.) · 2021Article
- Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.Chemical reviews · 2020Review
- Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates.Molecules (Basel, Switzerland) · 2020Review
- An overview on disulfide-catalyzed and -cocatalyzed photoreactions.Beilstein journal of organic chemistry · 2020Review
- Enantioselective cyanation via radical-mediated C-C single bond cleavage for synthesis of chiral dinitriles.Nature communications · 2019Article
- LightScience (New York, N.Y.) · 2019Article
- Molecular Dynamics Simulations of a Conformationally Mobile Peptide-Based Catalyst for Atroposelective Bromination.ACS catalysis · 2018Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
An enantioselective vinylcyclopropane ring-opening/cycloaddition cascade is described. The active thiyl radical catalysts are generated in situ via UV light-promoted homolysis of cystine-based dimers. Amide-functionalization of the peptide at the 4-proline position is essential for effective asymmetric induction. Stereochemical communication is dependent on steric interactions with this substituent that are enforced by H-bonding to the peptide backbone.
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Registered trials
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