ArticleThe Journal of organic chemistry2017
Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst.
Article in The Journal of organic chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Asymmetric Desymmetrizing Sulfonylation of Diarylmethanes via Peptidyl-Cu(I)-Catalysis with Remote Stereocontrol.Journal of the American Chemical Society · 2026Article
- An Asymmetric Aromatic Finkelstein Reaction: A Platform for Remote Diarylmethane Desymmetrization.Journal of the American Chemical Society · 2023Article
- Catalytic Asymmetric Hydrogen Atom Transfer: Enantioselective Hydroamination of Alkenes.Journal of the American Chemical Society · 2023Article
- Stapled β-Hairpins Featuring 4-Mercaptoproline.Journal of the American Chemical Society · 2021Article
- Catalytic Enantioselective Synthesis of Pyridyl Sulfoximines.Journal of the American Chemical Society · 2021Article
- Access toChemical science · 2021Article
- Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.Chemical reviews · 2020Review
- Catalytic Enantioselective PyridineJournal of the American Chemical Society · 2019Article
- Terahertz Spectroscopy of Tetrameric Peptides.The journal of physical chemistry letters · 2019Article
- Disparate Catalytic Scaffolds for Atroposelective Cyclodehydration.Journal of the American Chemical Society · 2019Article
- Peptide-Based Catalysts Reach the Outer Sphere through Remote Desymmetrization and Atroposelectivity.Accounts of chemical research · 2019Article
- Phosphothreonine (pThr)-Based Multifunctional Peptide Catalysis for Asymmetric Baeyer-Villiger Oxidations of Cyclobutanones.ACS catalysis · 2019Article
- Enantioselective remote meta-C-H arylation and alkylation via a chiral transient mediator.Nature · 2018Article
- Enantioselective Desymmetrization of Methylenedianilines via Enzyme-Catalyzed Remote Halogenation.Journal of the American Chemical Society · 2018Article
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4 authors.
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Abstract
Diarylmethylamido bis(phenols) have been subjected to peptide-catalyzed, enantioselective bromination reactions. Desymmetrization of compounds in this class has been achieved such that enantioenriched products may be isolated with up to 97:3 er. Mechanistically, the observed enantioselectivity was shown to be primarily a function of differential functionalization of enantiotopic arenes, although additional studies unveiled a contribution from secondary kinetic resolution of the product (to afford the symmetrical dibromide) under the reaction conditions. Variants of the tetrapeptide catalyst were also evaluated and revealed a striking observation-enantiodivergent catalysis is observed upon changing the achiral amino acid residue in the catalyst (at the i+2 position) from an aminocyclopropane carboxamide residue (97:3 er) to an aminoisobutyramide residue (33:67 er) under a common set of conditions. An expanded set of catalysts was also evaluated, enabling structure/selectivity correlations to be considered in a mechanistic light.
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