Hydroalumination and related reactions of phenyl 1-(trimethylsilyl)propadienyl sulfide followed by quenching with carbonyl compounds

Phenyl 1-(trimethylsilyl)propadienyl sulfide undergoes a hydroalumination with diisobutylaluminum hydride (DIBAH) or lithium butyl(diisobutyl)aluminum hydride (BL-DIBAH). The adduct anion derived from DIBAH is regioselectively trapped with carbonyl compounds at the position α to the phenylthio moiety to give 1,3-dienes as Peterson olefination products; the anion derived from BL-DIBAH is trapped at the position γ to the phenylthio moiety to give 3-buten-1-ols. Silylmetalation and stanylalumination on the same acceptor have been also briefly investigated as equivalent reactions.