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Synlett 1996; 1996(12): 1155-1158
DOI: 10.1055/s-1996-5706
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Cycloadditions of Allylsilanes, Part 8.1 Diastereoselective Synthesis of Spirocyclopentanes by Lewis Acid Promoted [3+2] Cycloaddition of Allyltriisopropylsilane and 2-Alkylidenecycloalkan-1-ones

Hans-Joachim Knölker* , Peter G. Jones, Regina Graf
  • *Institut für Organische Chemie, Universität Karlsruhe, Richard-Willstätter-Allee, D-76131 Karlsruhe, Germany, Fax +49(721)698-529; E-mail: knoe@ochhades.chemie.uni-karlsruhe.de
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Publikationsdatum:
31. Dezember 2000 (online)

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The reaction of the titanium tetrachloride complexes of 2-alkylidenecycloalkan-1-ones with allyltriisopropylsilane is highly stereospecific at low temperatures and provides a simple direct access to spirocyclic ring systems. The method is extended to the synthesis of polyspiranes.

allyltriisopropylsilane - spiroannulations - diastereoselectivity - silylcyclopentanes - polyspiranes