ArticleChemical science2022
Dynamic kinetic resolution of transient hemiketals: a strategy for the desymmetrisation of prochiral oxetanols.
Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Ring-Opening of Aziridines Using Tethered Hemiketals.The Journal of organic chemistry · 2026Article
- Ring opening of photogenerated azetidinols as a strategy for the synthesis of aminodioxolanes.Beilstein journal of organic chemistry · 2024Article
- Enantioenriched 1,4-Benzoxazepines via Chiral Brønsted Acid-Catalyzed Enantioselective Desymmetrization of 3-Substituted Oxetanes.The Journal of organic chemistry · 2023Article
- Transient Formation of Hemiketals from Pentafluoro-Journal of fluorine chemistry · 2023Article
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Authors and funding
5 authors.
Funding
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Abstract
Identification of an electron poor trifluoroacetophenone allows the formation of uniquely stable hemiketals from prochiral oxetanols. When exposed to a cobalt(ii) catalyst, efficient ring-opening to densely functionalized dioxolanes is observed. Mechanistic studies suggest an unprecedented redox process between the cobalt(ii) catalyst and the hemiketal that initiates the oxetane-opening. Based on this observation, a dynamic kinetic resolution of the transient hemiketals is explored that uses a Katsuki-type ligand for stereoinduction (up to 99 : 1 dr and 96 : 4 er) and allows a variety of 1,3-dioxolanes to be accessed (20 examples up to 98% yield).
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Registered trials
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