Indium-catalysed ring opening of 2-hydroxybutyrolactone through the cleavage of C(sp 3 )–O bond
Résumé
The ring-opening by the cleavage of the C(sp 3)-O bond of 2-hydroxybutyrolactone with (ethylthio)trimethylsilane was effectively catalysed by indium triiodide. Screening the reaction conditions allowed optimizing the ring-opening. The effect of the nucleophile/catalyst ratio on the reaction efficiency has also been demonstrated. After optimization, 2-hydroxy-4-(ethylthio)butyric acid was isolated with an excellent yield (85%), thus making this method useful for the preparation of methionine analogues.
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