ArticleJournal of the American Chemical Society2022
Enantioselective Giese Additions of Prochiral α-Amino Radicals.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
What it found
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
7 citing papers in PubMed.
- Acyl-oxyallenes as α,β-unsaturated ketone surrogates for Giese radical addition.Chemical science · 2026Article
- Monofluoromethyl Radical Mediated Halogen-Atom Transfer.Journal of the American Chemical Society · 2025Article
- Asymmetric cyanoesterification of vinylarenes by electrochemical copper catalysis.Nature communications · 2025Article
- Photoredox-catalyzed C(Science advances · 2024Article
- Oxidative Cross Dehydrogenative Coupling ofJournal of the American Chemical Society · 2023Article
- Discovery and Development of the Enantioselective Minisci Reaction.Accounts of chemical research · 2023Article
- Computational molecular refinement to enhance enantioselectivity by reinforcing hydrogen bonding interactions in major reaction pathway.Chemical science · 2023Article
Corrections and comments
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Amines featuring an adjacent stereocenter are important building blocks, and recent years have seen remarkable growth in methods forming these via prochiral α-amino radical intermediates. However, very few can exert control over the newly formed stereocenter. We disclose a strategy to overcome this in the context of one of the most widely used radical carbon-carbon bond forming reactions, the Giese reaction. Incorporation of a removable basic heteroarene into the substrate enables a network of attractive noncovalent interactions between a phosphoric acid catalyst, the subsequently formed α-amino radical, and the Giese acceptor, allowing the catalyst to exert control during the C-C bond forming step. Deprotection of the products leads to analogues of γ-aminobutyric acid. We anticipate that this strategy will be applicable to other asymmetric radical transformations in which catalyst control is presently challenging.
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Registered trials
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