An Unprecedented Ring Transformation of a 4-(Aminomethyl)oxazoline Derivative to a 4-(Hydroxymethyl)imidazoline

Abstract

An optically active 4-(azidomethyl)-2-(2-pyridyl)oxazoline was prepared starting from l-serine and picolinic acid. Reduction of the azide moiety gave the corresponding 4-(aminomethyl)-2-(2-pyridyl)oxazoline, which is not a stable compound but readily undergoes ring-transformation rearrangement to furnish a 4-(hydroxymethyl)-2-(2-pyridyl)imidazoline. After Boc protection of the amidine function, the material could be further converted into the 4-(aminomethyl)-2-(2-pyridyl)imidazoline via the respective azidomethyl compound.

Key words

heterocycles - oxazolines - imidazolines - pyridines - chiral ligands

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