Biocatalytic Silylation: The Condensation of Phenols and Alcohols with Triethylsilanol

Silicatein-? (Sil?), a hydrolytic enzyme derived from siliceous marine sponges, is one of the few enzymes in nature capable catalysing metathesis silicon–oxygen bonds. It therefore interest as possible biocatalyst for synthesis organosiloxanes. To further investigate substrate scope this enzyme, series condensation reactions with variety phenols and aliphatic alcohols were carried out. In general, it was observed that Sil? demonstrated preference phenols, though conversions relatively modest most cases. two pairs chiral investigated, found displayed silylation S-enantiomers. Additionally, enzyme’s tolerance to range solvents tested. had highest level conversion nonpolar n-octane toluene, although inclusion up 20% 1,4-dioxane tolerated. These results suggest potential candidate directed evolution toward future application robust selective organosiloxane chemistry.