1,2-Addition of dimethyl(phenyl)silyllithium to cyclic α,β-unsaturated ketones and regiospecific generation of cyclic silyl enol ethers through Brook rearrangement of the 1,2-addition products

Article abstract of DOI:10.1016/S0040-4039(00)94639-2

A highly convenient two-step sequence for the regiospecific synthesis of cyclic silyl enol ethers has been developed involving the 1,2-addition of dimethyl(phenyl)silyllithium to cyclic α,β-unsaturated ketones followed by the treatment of the resulting silyl carbinols with a catalytic amount of NaH in THF at 25°C.