Synthesis of silyloxyvinylstannanes from BHT ester enolates and stannyllithium reagents. Copper(I)-mediated coupling with alkenyl halides

The synthesis of silyloxyvinylstannanes was achieved via reaction of BHT es ter enolates with tributylstannyllithium and trapping of the resulting enol ates with phenyldimethylchlorosilane. They were coupled with alkenyl iodide s through a Cu(I)-mediated reaction to generate silyl dienol ethers which w ere readily transformed into alpha.beta -unsaturated ketones.