Allylsilanes derived from α- and β-ionone. Synthesis and unusual reactivity with electrophiles

Article abstract of DOI:10.1016/S0040-4039(01)93856-0

Silylcupration of α- and β-ionol acetates selectively gave the corresponding allylsilanes with direct substitution of the acetate with a trimethylsilyl group. Reactions of these products with electrophiles showed the unusual absence of the allylic shift, typical in nucleophilic condensations of allylsilanes. Ionotrimethylsilanes are effective building blocks for synthesis of terpenes and carotenoids.