A facile approach to C-functionalized β-ketoimine compounds via terminal alkylation of a tetralithiated intermediate

A series of C-functionalized β-ketoimine compounds at the terminal methyl groups of the β-ketoimine precursor LphH2 (Lph = C6H4[NC(Me)CHC(Me)O]2) were prepared. This convenient transformation was realized via straightforward double alkylation on the terminal Cα of a novel bis-dianionic β-ketoiminate lithium complex [Lph'Li4(THF)4]2 (Lph' = C6H4[NC(Me)CHC(O)CH2]2) followed by hydrolysis.