ArticleJournal of the American Chemical Society2020
Highly Enantioselective, Hydrogen-Bond-Donor Catalyzed Additions to Oxetanes.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed, 73 citations in OpenAlex.
- Oxetane-to-azetidine skeletal editing.Nature chemistry · 2026Article
- Atroposelective Bromination for the Synthesis of Chiral Biaryl Phosphines via Cross-Assembled Catalysis with Chiral Phosphoric Acid and Achiral Phenol.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
- Article
- Chiral Hydrogen-Bond Donor and Gold(I) Cocatalysis Enables Enantioselective Dearomative Spirocyclization of Naphthols.Journal of the American Chemical Society · 2025Article
- Enantioselective Desymmetrization by Chiral Bifunctional H-Bonding Organocatalysts.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- The impact of supramolecular self-association of organocatalysts on catalytic performance.Nature reviews. Chemistry · 2025Review
- Oxetanes: formation, reactivity and total syntheses of natural products.Beilstein journal of organic chemistry · 2025Review
- Synergistically activating nucleophile strategy enabled organocatalytic asymmetric P-addition of cyclic imines.Chemical science · 2024Article
- Enantioenriched 1,4-Benzoxazepines via Chiral Brønsted Acid-Catalyzed Enantioselective Desymmetrization of 3-Substituted Oxetanes.The Journal of organic chemistry · 2023Article
- Short and Efficient Synthesis of the Antituberculosis Agent Pretomanid from (Organic process research & development · 2023Article
- Exploring Structure-Function Relationships of Aryl Pyrrolidine-Based Hydrogen-Bond Donors in Asymmetric Catalysis Using Data-Driven Techniques.ACS catalysis · 2022Article
- Recent Progress in the Synthesis of Drugs and Bioactive Molecules Incorporating Nitro(het)arene Core.Pharmaceuticals (Basel, Switzerland) · 2022Review
- Efficient access to general α-tertiary amines via water-accelerated organocatalytic multicomponent allylation.Nature communications · 2022Article
- Bioinspired Cobalt-Catalysis Enables Generation of Nucleophilic Radicals from Oxetanes.Organic letters · 2022Article
- Hydrogen Bonding Phase-Transfer Catalysis with Alkali Metal Fluorides and Beyond.Journal of the American Chemical Society · 2022Article
- Enantioselective catalytic 1,2-boronate rearrangements.Science (New York, N.Y.) · 2021Article
- A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Brønsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings.Journal of the American Chemical Society · 2021Article
- Enantioselective, Catalytic Multicomponent Synthesis of Homoallylic Amines Enabled by Hydrogen-Bonding and Dispersive Interactions.Journal of the American Chemical Society · 2021Article
- Recent Advances in Enantioselective Desymmetrizations of Prochiral Oxetanes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
A precisely designed chiral squaramide derivative is shown to promote the highly enantioselective addition of trimethylsilyl bromide (TMSBr) to a broad variety of 3-substituted and 3,3-disubstituted oxetanes. The reaction provides direct and general access to synthetically valuable 1,3-bromohydrin building blocks from easily accessed achiral precursors. The products are readily elaborated both by nucleophilic substitution and through transition-metal-catalyzed cross-coupling reactions. The enantioselective catalytic oxetane ring opening was employed as part of a three-step, gram-scale synthesis of pretomanid, a recently approved medication for the treatment of multidrug-resistant tuberculosis. Heavy-atom kinetic isotope effect (KIE) studies are consistent with enantiodetermining delivery of bromide from the H-bond-donor (HBD) catalyst to the activated oxetane. While the nucleophilicity of the bromide ion is expected to be attenuated by association to the HBD, overall rate acceleration is achieved by enhancement of Lewis acidity of the TMSBr reagent through anion abstraction.
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Registered trials
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.