Diels-Alder Reactions of Siloxyallylidenecyclopropanes: Facile Syntheses of Spiro[2.5]Octan-3-Ones

  • Thies Thiemann
  • Stephan Kohlstruk
  • Gerhard Schwär
  • Armin de Meijere
Part of the NATO ASI Series book series (ASIC, volume 273)


Although 1,1-disubstituted dienes are known to be quite unreactive in Diels-Alderreactions, allylidenecyclopropanes due to the strain inherent in their methylenecyclopropane moiety have been found to react smoothly with activated enes.1,2b Moreover, it has been shown that the spirocyclopropane group in the cycloadducts can be reduced to a gem-dimethyl While such cycloadditions have been done with unsubstituted allylidenecyclopropane,1 and recently also a 3-heterosubstituted allylidenecyclopropane has been synthesized,2 a 2-heterosubstituted analog has not been reported to our knowledge. The 2-trialkylsiloxyallylidenecyclopropanes 2 can easily be prepared by silylenolization3 from the readily available cyclopropylideneketones l.4


Physical Chemistry Organic Chemistry Good Yield Thermal Condition Limited Length 
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Copyright information

© Kluwer Academic Publishers 1989

Authors and Affiliations

  • Thies Thiemann
    • 1
  • Stephan Kohlstruk
    • 1
  • Gerhard Schwär
    • 1
  • Armin de Meijere
    • 1
  1. 1.Institut für Organische Chemieder Universitat HamburgHamburg 13West-Germany

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