Generation of ketone dilithio α,β-dianions and their reactions with electrophiles

Ketone dilithio α,β- and α,β′-dianions can be generated by a tin–lithium exchange reaction of the lithium enolate of β-tributyltin substituted ketones. A chelation-aided approach, which employs β-dichlorobutyltin substituted ketones and n-BuLi, is also useful for the generation of ketone α,β-dianions having the Z-geometry at the alkene. The generated dianions can be transformed into substituted ketones by reaction with various carbon electrophiles.