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Synlett 1990; 1990(12): 769-770
DOI: 10.1055/s-1990-21246
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Preparation and Alkylation Reactions of α-Chloroallyl Anion with Electrophiles

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

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Deprotonation of allyl chloride with lithium diisopropylamide (LDA) at low temperature gives a red solution of α-chloroallyllithium. The condensation with various electrophiles (alkyl halides, aldehydes, boric acid esters, Me3SiCl, Bu3SnCl) is described and the regioselectivity (α vs γ) is discussed.