| We have studied on developing new method for the generation of optically active alpha-hydroxysilanes. The ring opening of epoxy alcohols bearing a TMS group with both aluminum and boron hydrides provided the unfavoured 1,2-diol. This result shows that silicon plays an important role in determining the regioselectivity and that cyclic boronic esters are formed in the ring opening reaction. The scope and limitation of enzymatic kinetic resolution of ahydroxysilanes in combination with different solvents, temperatures and acetylation reagents were investigated. The reactions are sensitive to the structures of both the silyl group and the organic side chain. In the non enzymatic kinetic resolution, the absolute stereochemical outcomes complement our enzymatic results. |
