Indium-catalysed ring opening of 2-hydroxybutyrolactone through the cleavage of C(sp 3 )–O bond - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Comptes Rendus. Chimie Année : 2023

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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Dates et versions

hal-04354097 , version 1 (19-12-2023)

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Citer

Sameh Aoun, Joe Massouh, Noémie Scornet, Laurent Giordano, Alphonse Tenaglia, et al.. Indium-catalysed ring opening of 2-hydroxybutyrolactone through the cleavage of C(sp 3 )–O bond. Comptes Rendus. Chimie, 2023, 26 (G1), pp.89-98. ⟨10.5802/crchim.245⟩. ⟨hal-04354097⟩
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