Organic Letters· 2026Q1
Controlled Epoxide-Enabled Formal Oxygen Insertion of Indenones to Isocoumarins
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- 2026year
Short summary
A new two-step method converts indenones to isocoumarins via epoxide intermediates, achieving regioselective oxygen insertion without relying on migratory aptitude.
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Key points
- A two-step sequence converts indenones to isocoumarins using an epoxide intermediate.
- The method achieves regioselective oxygen insertion, bypassing migratory aptitude limitations.
- The process is compatible with diverse substituents and avoids overoxidation.
- It offers an alternative to direct m-CPBA oxidation of indenones.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract Regioselective oxygen insertion into sp2-rich carbonyl scaffolds remains challenging because Baeyer–Villiger oxidation relies on migratory aptitude. Here, we translate an aziridine-based nitrogen-insertion platform to an epoxide-enabled oxygen-insertion manifold for indenones. H2O2/NaOH epoxidation followed by MeSO3H-promoted rearrangement affords isocoumarins as single observed regioisomers in a two-step sequence. The method tolerates diverse substituents, enables orthogonal and sequential editing of distinct carbonyl motifs, and circumvents incomplete conversion and overoxidation encountered under direct m-CPBA conditions.
The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry