Figure 5. Applications of the silylation reaction protocol.
(a) Gram-scale kinetic resolution of secondary alcohol 2a using 1 p.p.m. of catalyst: The reactions were performed in the presence of 0.5 equiv of KF and 0.2 equiv of Amberlite CG 50 (CG 50). *Calculated conversion, c=ee(R)−2a/(ee(R)−2a+ee(S)−3a). †Isolated yields. (b) Catalytic enantioselective silylation of meso-diols 4 (0.1 mmol scale): The reactions were performed in the presence of 1 equiv of KF and 0.6 equiv of Amberlite CG 50 (CG 50). ‡The conversion was determined by 1H-NMR. †Isolated yields. §The reaction was performed at 0 °C. DCE, 1,2-dichloroethane; e.r., enantiomeric ratio.