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Synlett 1992; 1992(4): 329-331
DOI: 10.1055/s-1992-22003
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Michael-Type Addition of Carbocuprates to Acetylenic Silyl Ketone: A New Entry to Stereodefined Polyenes

Alessandro Degl'Innocenti* , Enrico Stucchi, Antonella Capperucci, Alessandro Mordini, Gianna Reginato, Alfredo Ricci
  • *Centro C.N.R. Composti Eterociclici, via G. Capponi 9, I-50121 Firenze, Italy
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Publication Date:
08 March 2002 (online)

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Ethynyl triphenylsilyl ketone (1) reacts smoothly with various carbocuprates, affording 3-functionalized propenoylsilanes. When using unsaturated carbocuprates, dienoylsilanes 2d-f are obtained. These synthetic equivalents of dienals can further react under Wittig conditions to afford a new and stereodefined entry into the class of silylated polyenes 4.

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