One-pot synthesis of α,β-unsaturated ketones from tert- butyldimethylsilyldibromomethane and two different aldehydes

Article abstract of DOI:10.1016/S0040-4039(00)73086-3

An addition of benzaldehyde to an ethereal solution of tert- butyldimethylsilyldibromomethyllithium provided α-bromo-α-silyl ketone. Further treatment of the α-bromo-α-silyl ketone with butyllithium afforded enolate which provided β-hydroxy-α-silyl ketone upon treatment with aldehyde in ether. The enolate gave α,β-unsaturated ketone or monosilyl ether or 2-acyl-1,3-diol in THF instead of ether.