Indium-catalysed ring opening of 2-hydroxybutyrolactone through the cleavage of C(sp$^3$)–O bond
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 effici...
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| Format: | Article |
| Language: | English |
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Académie des sciences
2023-09-01
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| Series: | Comptes Rendus. Chimie |
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| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.245/ |
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| author | Aoun, Sameh Massouh, Joe Scornet, Noémie Giordano, Laurent Tenaglia, Alphonse Buono, Gérard Rey, Patrick Bellière-Baca, Virginie Hérault, Damien |
| author_facet | Aoun, Sameh Massouh, Joe Scornet, Noémie Giordano, Laurent Tenaglia, Alphonse Buono, Gérard Rey, Patrick Bellière-Baca, Virginie Hérault, Damien |
| author_sort | Aoun, Sameh |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-32b427c3041e42e3a333a1b7bf69d3da |
| institution | Kabale University |
| issn | 1878-1543 |
| language | English |
| publishDate | 2023-09-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj-art-32b427c3041e42e3a333a1b7bf69d3da2025-02-07T13:38:00ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432023-09-0126G1899810.5802/crchim.24510.5802/crchim.245Indium-catalysed ring opening of 2-hydroxybutyrolactone through the cleavage of C(sp$^3$)–O bondAoun, Sameh0Massouh, Joe1Scornet, Noémie2Giordano, Laurent3Tenaglia, Alphonse4Buono, Gérard5https://orcid.org/0000-0001-8505-4005Rey, Patrick6Bellière-Baca, Virginie7Hérault, Damien8https://orcid.org/0000-0001-7753-3276Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceAix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceAix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceAix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceAix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceAix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceAdisseo France SAS, Antony Parc 2, 10 Place du Général de Gaulle, 92160 Antony, FranceAdisseo France SAS, Antony Parc 2, 10 Place du Général de Gaulle, 92160 Antony, FranceAix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceThe 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.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.245/MethionineLactoneSulfur nucleophilesIndiumThiol |
| spellingShingle | Aoun, Sameh Massouh, Joe Scornet, Noémie Giordano, Laurent Tenaglia, Alphonse Buono, Gérard Rey, Patrick Bellière-Baca, Virginie Hérault, Damien Indium-catalysed ring opening of 2-hydroxybutyrolactone through the cleavage of C(sp$^3$)–O bond Comptes Rendus. Chimie Methionine Lactone Sulfur nucleophiles Indium Thiol |
| title | Indium-catalysed ring opening of 2-hydroxybutyrolactone through the cleavage of C(sp$^3$)–O bond |
| title_full | Indium-catalysed ring opening of 2-hydroxybutyrolactone through the cleavage of C(sp$^3$)–O bond |
| title_fullStr | Indium-catalysed ring opening of 2-hydroxybutyrolactone through the cleavage of C(sp$^3$)–O bond |
| title_full_unstemmed | Indium-catalysed ring opening of 2-hydroxybutyrolactone through the cleavage of C(sp$^3$)–O bond |
| title_short | Indium-catalysed ring opening of 2-hydroxybutyrolactone through the cleavage of C(sp$^3$)–O bond |
| title_sort | indium catalysed ring opening of 2 hydroxybutyrolactone through the cleavage of c sp 3 o bond |
| topic | Methionine Lactone Sulfur nucleophiles Indium Thiol |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.245/ |
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