ArticleJournal of the American Chemical Society2021
A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Brønsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 51 citations in OpenAlex.
- Oxetane-to-azetidine skeletal editing.Nature chemistry · 2026Article
- Catalytic Enantioselective Aziridination of Z-Disubstituted Alkenes with Aspartyl β-Turn-Based Dirhodium(II) Metallopeptides and Assessment of Catalyst Scaffold Versatility.Journal of the American Chemical Society · 2026Article
- Recognition of a Conserved Minimal Catalaphile Explains Catalyst Generality in Enantioselective Nitroalkene Reductions.ACS catalysis · 2026Article
- Assessment of Complementary Catalysts in an Uncharted Enantioselective Reaction of Sulfondiimines.Journal of the American Chemical Society · 2026Article
- Leveraging Lewis acid catalysis for cascade construction of multisubstituted furans from active methylenes and 3-oxetanone.Communications chemistry · 2026Article
- E/Z Isomerization-Enabled Conversion from Dual-Carbon to Single-Carbon Insertion into an Aromatic System.JACS Au · 2026Article
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- Experimental Lineage and Computational Analysis of a General Aminoxyl-Based Oxidation Catalyst: Generality from Substrate-Specific Interactions.ACS catalysis · 2025Article
- Ureas and Their Derivatives as Ligands in Transition Metal Catalysis.Tetrahedron · 2025Article
- Privileged Chiral Photocatalysts.Angewandte Chemie (International ed. in English) · 2025Review
- Enantioselective Ring Opening of Azetidines via Charge Recognition in Hydrogen-Bond-Donor Catalysis.Journal of the American Chemical Society · 2025Article
- On the gold(I)-catalyzed enantioselective addition of indole to diphenylallene via anion-binding catalysis.Tetrahedron letters · 2024Article
- A genetic optimization strategy with generality in asymmetric organocatalysis as a primary target.Chemical science · 2024Article
- Generality-Driven Catalyst Development: A Universal Catalyst for Enantioselective Nitroalkene Reduction.Journal of the American Chemical Society · 2024Article
- Machine learning-guided strategies for reaction conditions design and optimization.Beilstein journal of organic chemistry · 2024Review
- Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis.Beilstein journal of organic chemistry · 2024Review
- All-round catalytic and atroposelective strategy via dynamic kinetic resolution for N-/2-/3-arylindoles.Nature communications · 2023Article
- Generality-oriented optimization of enantioselective aminoxyl radical catalysis.Science (New York, N.Y.) · 2023Article
- Molecular Understanding and Practical In Silico Catalyst Design in Computational Organocatalysis and Phase Transfer Catalysis-Challenges and Opportunities.Molecules (Basel, Switzerland) · 2023Review
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Authors and funding
4 authors at 1 institution in 1 country.
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Abstract
Generality in asymmetric catalysis can be manifested in dramatic and valuable ways, such as high enantioselectivity across a wide assortment of substrates in a given reaction (broad substrate scope) or as applicability of a given chiral framework across a variety of mechanistically distinct reactions (privileged catalysts). Reactions and catalysts that display such generality hold special utility, because they can be applied broadly and sometimes even predictably in new applications. Despite the great value of such systems, the factors that underlie generality are not well understood. Here, we report a detailed investigation of an asymmetric hydrogen-bond-donor catalyzed oxetane opening with TMSBr that is shown to possess unexpected mechanistic generality. Careful analysis of the role of adventitious protic impurities revealed the participation of competing pathways involving addition of either TMSBr or HBr in the enantiodetermining, ring-opening event. The optimal catalyst induces high enantioselectivity in both pathways, thereby achieving precise stereocontrol in fundamentally different mechanisms under the same conditions and with the same chiral framework. The basis for that generality is analyzed using a combination of experimental and computational methods, which indicate that proximally localized catalyst components cooperatively stabilize and precisely orient dipolar enantiodetermining transition states in both pathways. Generality across different mechanisms is rarely considered in catalyst discovery efforts, but we suggest that it may play a role in the identification of so-called privileged catalysts.
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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.