3-​Trimethylsilylbicyclo[3.2.1]​oct-​2-​ene in the synthesis of functionalized bicyclo[3.2.1]​octane systems

(bicyclo[3.2.1]​oct-​2-​en-​3-​yl)​trimethylsilane (3-​trimethylsilylbicyclo[3.2.1]​oct-​2-​ene) is shown to be useful in the synthesis of functionalized bicyclo[3.2.1]​octanes. It undergoes acylation to give 3-​bicyclo[3.2.1]​oct-​2-​enyl ketones without undergoing skeletal rearrangement, in contrast to the acylation of 2-​trimethylsilylbicyclo[2.2.1]​hept-​2-​ene. It can be epoxidized and an epoxysilane, hydrolyzes to a silyldiol in a normal way as against the resistance of 2-​trimethylsilylbicyclo[2.2.1]​hept-​2-​ene epoxide towards hydrolysis