Allylation reactions of acylsilanes as synthetic equivalents of aldehydes. Application to a stereocontrolled synthesis of (1S,2S,5S)-(10S)-and-(10R)-allyl myrtanol

The allylation of acylsilanes with tetraallyltin in the presence of catalytic amounts of Sc(OTf) 3 proceeded smoothly to afford the silylated homoallylic alcohols in good yields. Subsequent protiodesilylation gave the formal adducts of the corresponding aldehydes. The homochiral acylsilane 11 gave a reversal of asymmetric induction in the Sc(OTf) 3 catalyzed allylation and in the Sakurai reaction.