This project aimed at developing efficient symmetric and asymmetric hydroboration-oxidation protocols for silyl enol ethers. The hydroboration of enol ethers is a synthetic approach to anti-diols. The hypothesis is that silyl enol ethers, which become traceless after fluoride workup, should provide diols in excellent yields upon hydroboration-oxidation. However, before the start of this project, there was just one published report on the unsuccessful development of this methodology using trimethyl silane as protecting group (https://doi.org/10.1016/S0022-328X(00)90309-7). The project aimed to reexamine this protocol, examine the use of other silyl protecting groups, and, if necessary, explore the use of catalysts to achieve the synthesis. We completed the first and second objectives over the summer where we observed that the non-catalyzed hydroboration of silyl enol ethers only provided the diols in very low yields, irrespective of the silyl protecting group. The direct reduction product and the 1,2-transposed alcohol products were dominant. At this point, the summer program ended.