Unsymmetrical alkyl 2-hydroxy-1-(1-hydroxyalkyl)alkyl ketones (bis-aldols) are successfully synthesized by way of sequential two aldol reactions using alpha -bromo ketones and two different aldehydes. In the first reaction, alpha -bromo-beta -stannyloxy ketones are formed by tin(II) trifluoromethanesulfomate-promoted aldol reaction of alpha -bromo ketones with several aldehydes. Bis-aldols are then formed via the second aldol reaction between another aldehydes and dianionic enolates generated by the reduction of alpha -bromo-beta -metalloxy ketones with titanium(IV) iodide and copper.