Dearomatization of anisole chromiumtricarbonyl by sequential regio- and diastereoselective addition of a C-nucleophile and a C-electrophile is problematic because of competitive ortho-deprotonation. A solution is offered by carrying out the reaction ­sequence with the bis ortho silylated complex. Decomplexation and acid work-up affords 4,5-trans-disubstituted cyclohexenones.