Phosphine catalyzed aldol reaction between ketene silyl acetals and aldehydes: nucleophilic O–Si and C–Si bond cleavage by phosphines

A highly nucleophilic phosphine, tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP), catalyzes the aldol reaction between ketene silyl acetals and aldehydes to give the corresponding aldol products in good to high yields. This reaction is considered to proceed through naked enolates produced by nucleophilic O–Si and C–Si bond cleavage.