STEREOSELECTIVE SYNTHESIS OF NEUTRAL AND CATIONIC 2-HETEROCYCLICALLY SUBSTITUTED PROPANAMIDES

Neutral 2-(1'-imidazolyl)-N-[(1'R)-phenylethyl]propanamide 5 and the r elated methylimidazolium and pyridinium salts 6-9 were easily prepared from 2-bromoamide la and imidazole, N-methylimidazole and pyridine at room temperature in toluene. The stereoselectivity was lower than wit h other nucleophiles, Ag+ and Ag2O proving less selective promoters, a nd Ag2O allowing racemization of starting material and side reactions to be observed. (C) 1997 Elsevier Science Ltd.