Enantioselective reactions of 2-bromopropanamides with primary secondary or tertiary amines. Synthesis of some alaninamides.

Enantiomeric 2-bromopropanamides react with primary, secondary, or tertiary aliphatic amines in toluene at room temperature, yielding the corresponding secondary or tertiary amino, or quaternary ammonium amide. If the reacting amines are good nucleophiles, either product is obtainable in high yield and e.e., by running the reaction either in the presence or absence of Ag2O. With a less nucleophilic amine, Ag2O or Ag+ promotes the formation either of an optically active amine derivative, or a high diastereomeric excess of a dimeric derivative, whose structure was ascertained by X-ray analysis. © 1991.