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Synthesis 1999; 1999(1): 145-151
DOI: 10.1055/s-1999-3684
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Cycloadditions of Allylsilanes, Part 12. Regio- and Stereoselective Transformations of Silylbicyclo[n.3.0]alkanes

Hans-Joachim Knölker* , Norbert Foitzik, Christoph Gabler, Regina Graf
  • *Institut für Organische Chemie, Universität Karlsruhe, Richard-Willstätter-Allee, D-76131 Karlsruhe, Germany; Fax +49(7 21)69 85 29; E-mail: knoe@ochhades.chemie.uni-karlsruhe.de
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Publication Date:
31 December 1999 (online)

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Lewis acid promoted [3 + 2] cycloaddition of 1-acetylcycloalkenes and allylsilanes provides the silylbicyclo[n.3.0]-alkanes 4 and 5. The sequence of regioselective Bayer-Villiger oxidation and elimination of acetic acid affords the 3-silylbicyclo[3.3.0]oct-1(5)-enes 8a and 9a and the 8-(triphenylsilyl)bicyclo[4.3.0]non-1(6)-ene (8b). Epoxidation and catalytic hydrogenation of these olefins proceeds with complete stereoselectivity anti relative to the silyl substituent. Ozonolysis of 8b leads to 3-(triphenylsilyl)cyclononane-1,5-dione (15).

allylsilanes - [3 + 2] cycloadditions - Bayer-Villiger oxidation - molecular modelling - diastereoselective epoxidation

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