b-Functionalized and a,b-Difunctionalized Ketones from 1-Arylallylic Alcohols via Dipotassio a,b-Dianion Intermediates

This study reports the synthesis of diverse b-functionalized ketones from readily available 1-arylallylic alcohols in the presence of (trimethylsilyl)methylpotassium (TMSCH2K). The reaction proceeded via the formation of the highly nucleophilic dipotassio a,b-dianion as the key intermediate, which served as a metal homoenolate equivalent. This protocol also allowed the one-pot synthesis of a,b-difunctionalized ketones using two different electrophiles, thus demonstrating its synthetic advantages over other protocols involving metal homoenolates.