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Synlett 1998; 1998(10): 1057-1058
DOI: 10.1055/s-1998-1896
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Stereospecific Cyclopropanation Reactions of Stannyl-Substituted Acetals with Alkenes via γ-Elimination of Tin

Masanobu Sugawara* , Jun-ichi Yoshida
  • *Department of Synthetic Chemistry and Biologcal Chemistry, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto 606-8501, Japan
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Publication Date:
31 December 2000 (online)

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The reactions of stannyl substituted acetals with olefins resulted in the elimination of both the triorganostannyl group and the alkoxy group on the same carbon, and the production of the corresponding alkoxycyclopropanes in good yields. The stereospecificity of the present reaction suggests that γ-elimination of tin is very fast.

cyclopropanation - Lewis acid - organostannane - γ-elimination of tin

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