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Synlett 1991; 1991(9): 647-648
DOI: 10.1055/s-1991-20827
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Vinyl Cyclopropanation of Alkenes with Allylic Halides

Ian Jefferies* , Marc Julia, Jean-Noël Verpeaux, Thomas Zahneisen
  • *Laboratoire de Chimie de l'École Normale Supérieure, 24 rue Lhomond, F-75231 Paris Cedex 05, France
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Publication Date:
07 March 2002 (online)

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Lithiated prenyl (2-methyl-2-butenyl) bromide or chloride, generated by in situ deprotonation of the halide, undergoes cyclopropanation of unactivated alkenes and enol ethers to give the corresponding (2-methyl-1-propenyl)cyclopropanes. This carbenoid reacts more readily with electron rich or highly substituted olefins, displaying an electrophilic behaviour.