One-Step Synthesis of Highly Functionalized Monofluorinated Cyclopropanes from Electron-Deficient Alkenes

One-Step Synthesis of Highly Functionalized Monofluorinated Cyclopropanes from Electron-Deficient Alkenes

The unique combination of Zn/LiCl allowed generation of reactive zinc enolate from ethyl dibromofluoroacetate. This fluorinated enolate reacts efficiently with a wide range of functionalized electron-deficient alkenes to afford the corresponding monofluorinated cyclopropylcarboxylates in good yields...

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Veröffentlicht in:Organic letters 2012-05, Vol.14 (9), p.2270-2273
Hauptverfasser: Ivashkin, Pavel, Couve-Bonnaire, Samuel, Jubault, Philippe, Pannecoucke, Xavier
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes - chemistry
Catalysis
Chemical Sciences
Combinatorial Chemistry Techniques
Cyclization
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Molecular Structure
Organic chemistry
Stereoisomerism
Zinc
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Beschreibung
Zusammenfassung:The unique combination of Zn/LiCl allowed generation of reactive zinc enolate from ethyl dibromofluoroacetate. This fluorinated enolate reacts efficiently with a wide range of functionalized electron-deficient alkenes to afford the corresponding monofluorinated cyclopropylcarboxylates in good yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300687s