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Synthesis 1990; 1990(5): 382-386
DOI: 10.1055/s-1990-26881
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Convenient Stereoselective Syntheses of (6E)- and (6Z)-5,6-Dimethyl-8-silyl-octenals

Kazuhiko Asao* , Hideo Iio, T. Tokoroyama
  • *Faculty of Science, Osaka City University, Sumiyoshi-ku, Osaka 558, Japan
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Publication Date:
17 September 2002 (online)

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A stereoselective synthetic method for the title compounds, E- and Z- allylsilanes, which would be generally applicable for the preparation of other trisubstituted allylsilanes, has been elaborated. The key steps are the following: (i) stereoselective preparation of (2Z)- and (2E)-3-[(diethoxy)phosphoryloxy]-2-octenoates (Z)- and (E)- 4, (ii) substitution of 3-phosphoryloxy group with methyl in the presence of palladium catalyst [(Z/E)-4 → (E/Z)-5]; and (iii) substitution reaction of the desired allyl chlorides with appropriate silyllithiums [(E/Z)-7 → (E/Z)-8].

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