Easy and Efficient Generation of Reactive Anions with Free and Supported Ylides as Neutral Brønsted Bases

The tris(dimethylamino)-C-dimethylphosphorus ylide 5 and the tris(dimethylamino)phosphorus ylide C-bound to Merrifieldʹs resin 6 are used as strong non-nucleophilic bases in N-alkylation reactions of β-amino phosphine oxides and α-amino acid derivatives, and in the C-alkylation reaction of enamines and benzophenone imines derived from glycine ethyl ester. Base-catalyzed aldol-type condensation (Henry) reaction of nitroethane with aldehydes and olefination reactions of phosphine oxides and phosphonates are also described.