Neutral (2R)-2-(1'-imidazolyl)-N-[(1'R)-phenylethyl]propanamide 5 and the related 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 with other nucleophiles, Ag+ and Ag2O proving less selective promoters, and Ag2O allowing racemization of starting material and side reactions to be observed.
Stereoselective synthesis of neutral and cationic 2-heterocyclically substituted propanamides
MARCHETTI, Paolo;BERTOLASI, Valerio
1997
Abstract
Neutral (2R)-2-(1'-imidazolyl)-N-[(1'R)-phenylethyl]propanamide 5 and the related 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 with other nucleophiles, Ag+ and Ag2O proving less selective promoters, and Ag2O allowing racemization of starting material and side reactions to be observed.File in questo prodotto:
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