ArticleTetrahedron2024
Intramolecular Oxyalkylation of Unactivated Alkenes.
Article in Tetrahedron, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
2 citing papers in PubMed.
- Preparation of a versatile fluorescence sensor for co-detecting ions in aqueous solution.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2026Article
- Oxyalkylation of Alkenes via Triple Radical Sorting.Journal of the American Chemical Society · 2026Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
The synthesis of cyclopropanes by the cyclization of allylic diazoesters is well-known. In prior studies toward the sesquiterpenoid euonyminol, we attempted to carry out an intramolecular cyclopropanation of an allylic diazoester containing an electronically-unbiased alkene embedded in a 6-oxa-bicyclo[3.2.1]-oct-3-ene skeleton. We obtained exclusively a product arising from 1,2-addition of oxygen and carbon (oxyalkylation) to the alkene. While oxyalkylation products have been reported when electron-rich alkenes (e.g. enol ethers) are employed, examples derived from electronically-unbiased alkenes are rare. Here, we establish that the oxyalkylation is general for a range of 6-oxa-bicyclo[3.2.1]-oct-3-ene substrates and show that these products form competitively in the cyclization of simpler α-diazo β-ketoesters. Our data suggest increasing charge separation in the transition state for the addition promotes the oxyalkylation pathway.
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Registered trials
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