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Synlett 1990; 1990(7): 429-430
DOI: 10.1055/s-1990-21118
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Conjugate Addition of Allylsilanes with Subsequent Sila-Wagner-Meerwein Rearrangement: A Novel Methodology for Stereoselective Trimethylsilylcyclopentane Annulation

Hans-Joachim Knölker* , Peter G. Jones, Jörn-Bernd Pannek
  • *Institut für Organische Chemie der Universität, Schneiderberg 1B, D-3000 Hannover 1, Federal Republic of Germany
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Publication Date:
08 March 2002 (online)

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A novel, stereoselective trimethylsilylcyclopentane annulation reaction is reported, in which conjugate addition of allyltrimethylsilane to 1-acetylcycloalkenes occurs with subsequent ß-silyl cation induced sila-Wagner-Meerwein rearrangement. It is suggested that the 1,2-silyl shift proceeds via an intermediate non-classical pentavalent silicon cation.