ArticleJournal of the American Chemical Society2023
Dual-Hydrogen-Bond Donor and Brønsted Acid Cocatalysis Enables Highly Enantioselective Protio-Semipinacol Rearrangement Reactions.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Catalytic Enantioselective Elimination of Cyclobutanols.Journal of the American Chemical Society · 2026Article
- Organo-catalyzed photoelectrochemical ring-contraction of arylidenecyclobutanolsChemical science · 2026Article
- Article
- Divergent Synthesis of Polycyclic N‑Heterocycles via Controllable Cyclization of Divinylallenes Catalyzed by Copper and Gold.JACS Au · 2025Article
- Stereospecific Synthesis of Cyclobutanones and Spirohexanones via Formal [3 + 1] Cycloaddition of Cyclopropanones with Sulfur Ylides.Organic letters · 2025Article
- Chiral sulfide and achiral sulfonic acid cocatalyzed enantioselective electrophilic tandem selenylation semipinacol rearrangement of allenols.Nature communications · 2025Article
- Enantioselective Synthesis of α-Aryl Ketones by a Cobalt-Catalyzed Semipinacol Rearrangement.Angewandte Chemie (International ed. in English) · 2025Article
- Catalytic asymmetric intramolecular propargylation of cyclopropanols to access the cuparane core.Chemical science · 2024Article
- Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
A catalytic protio-semipinacol ring-expansion reaction has been developed for the highly enantioselective conversion of tertiary vinylic cyclopropyl alcohols into cyclobutanone products bearing α-quaternary stereogenic centers. The method relies on the cocatalytic effect of a chiral dual-hydrogen-bond donor (HBD) with hydrogen chloride. Experimental evidence is provided for a stepwise mechanism where protonation of the alkene generates a short-lived, high-energy carbocation, which is followed by C-C bond migration to deliver the enantioenriched product. This research applies strong acid/chiral HBD cocatalysis to weakly basic olefinic substrates and lays the foundation for further investigations of enantioselective reactions involving high-energy cationic intermediates.
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Registered trials
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