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Synlett 1990; 1990(5): 270
DOI: 10.1055/s-1990-21060
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cis-2-Lithiated Enol Ethers: Preparation and Reactions with Electrophiles

José Barluenga* , Miguel A. Rodríguez, Pedro J. Campos
  • *Departamento de Química Organometálica, Universidad de Oviedo, E-33071 Oviedo, Spain
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Publication Date:
08 March 2002 (online)

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2-Isopropoxy-1-lithio-2-phenyl-1-alkenes are prepared by iodine-lithium exchange reactions of (Z)-1-iodo-2-isopropoxy-2-phenyl-1-alkenes and sec-butyl- or tert-butyllithium. These vinyllithium derivatives react with various electrophiles (methanol, deuterium oxide, iodomethane, phenylselenenyl bromide) to yield substituted enol ethers stereoselectively. The corresponding substituted acetophenones are obtained after acidic hydrolysis.