Stereoselective synthesis of a thiazolane amide using molecular recognition in the triazolyl-activated ester intermediate

An amide derived from penicillin V and racemic (R/S)-2-aminobutanol was prepared with 83% de and shows significantly higher toxicity than the pure diastereomers prepared from homochiral 2-aminobutanol. This has been attributed to conformational changes in the resolved product brought about through hydrogen-bonded self-assembly in the intermediate.