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1. Indium-catalysed ring opening of 2-hydroxybutyrolactone through the cleavage of C(sp$^3$)–O bond

Author

Aoun, Sameh, Massouh, Joe, Scornet, Noémie, Giordano, Laurent, Tenaglia, Alphonse, Buono, Gérard, Rey, Patrick, Bellière-Baca, Virginie, and Hérault, Damien

Subjects
Methionine, Lactone, Sulfur nucleophiles, Indium, Thiol, Biochemistry, QD415-436, Physical and theoretical chemistry, QD450-801, Mathematics, QA1-939
Abstract

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.

Published
2023
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