Abstract

Substituted trimethylsilyldienes 12a-14a were prepared in high yield and total stereocontrol using a metallate rearrangement induced by the reaction of the dilithiumbis-[(E)-2-(trimethylsilyl)ethenyl]cyanocuprate 11 with the 5-lithio-2,3-dihydrofuran 7-9. Trimethylsilyldienes 12-14 were then submitted to an electrophilic substitution in the presence of acetyl chloride and aluminium trichloride for an access to the corresponding dienones 15-22. Results were tentatively explained with the aid of a modeling study.

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