The substrate silanol epoxides could be conveniently prepared using one of two methods (Scheme 2). m-CPBA oxidation of the alkenyl silanol delivered the silanol epoxide in good yields, and, in our hands, this proved to be a very general procedure (Scheme 2A). As there is much technology for the stereocontrolled synthesis of epoxides from alkenyl alcohols, we reasoned that developing a method to attach the silanol auxiliary directly to epoxy-alcohols would be particularly impactful. Our standard silylating conditions failed to deliver product in reasonable yields with these particularly delicate substrates (Scheme 2B). We found that replacing DMAP with two equivalents of NaHCO3 and dropping the initial reaction temperature to -40 °C allowed for silanol epoxide formation reproducibly and in much better yields (Scheme 2B).