Easy and efficient generation of reactive anions with free and supported ylides as neutral Bronsted bases

The tris(dimethylamino)-C-dimethylphosphorus ylide 5 and the tris(dimethyla mino)phosphorus ylide C-bound to Merrifield's resin 6 are used as strong no n-nucleophilic bases in N-alkylation reactions of beta-amino phosphine oxid es and alpha-amino acid derivatives, and in the C-alkylation reaction of en amines and benzophenone imines derived from glycine ethyl ester. Base-catal yzed aldol-type condensation (Henry) reaction of nitroethane with aldehydes and olefination reactions of phosphine oxides and phosphonates are also de scribed. (C) 2000 Elsevier Science Ltd. All rights reserved.