ArticleOrganic letters2020
Substituted α-Alkylidene Cyclopentenones via the Intramolecular Reaction of Vinyl Cations with Alkenes.
Article in Organic letters, 2020. 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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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
4 citing papers in PubMed.
- B(CRSC advances · 2022Article
- DFT Mechanistic Study of the Cyclopropanation of Styrene and Aryldiazodiacetate Catalyzed by Tris(pentafluorophenyl)borane.ACS omega · 2022Article
- Solvent-controlled photocatalytic divergent cyclization of alkynyl aldehydes: access to cyclopentenones and dihydropyranols.Chemical science · 2021Article
- A Conjugate Addition Approach to Diazo-Containing Scaffolds with β Quaternary Centers.Angewandte Chemie (International ed. in English) · 2020Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Substituted α-alkylidene cyclopentenones are formed in up to 93% yield by the intramolecular capture of vinyl cations with pendent alkenes. An increased level of substitution at the β-position of the β-hydroxy-α-diazoketone starting material changed the course of the reaction to instead give a lactone product. A reaction path that involves bond reorganization via an acylium ion intermediate is proposed to explain these results. Substrate scope studies showed that more stable vinyl cations gave higher α-alkylidene cyclopentenone yields. This study provides a mild and efficient method to form α-alkylidene cyclopentenones that complements C-H insertion and Nazarov cyclization strategies.
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