Diastereoselective deacylative aldol reaction 
of 3-acetyl-3-fluorooxindoles with aldehydes
Sempere, Inmaculada ; Molina, Cynthia ; García-Mingüens, Eduardo ; Retamosa, Mª de Gracia ; Nájera, Carmen ; Merino, Pedro (Universidad de Zaragoza) ; Yus, Miguel ; Sansano, José M.
Resumen: The deacetylative aldol reaction of N-methyl-3-acetyl-3-fluoro-2-oxindole is optimized with benzaldehyde and the most appropriate conditions are used for the survey of the scope of this transformation with different aldehydes. The relative configuration of the resulting compounds is also confirmed. The reaction is diastereoselective and affords the syn-stereoisomer in good yields. DFT calculations are used for the explanation of this diastereoselectivity through a traditional chair-like transition state.
Idioma: Inglés
DOI: 10.24820/ark.5550190.p011.804
Año: 2022
Publicado en: ARKIVOC 2023, 3 (2022), 16-32
ISSN: 1551-7004
Factor impacto JCR: 0.9 (2022)
Categ. JCR: CHEMISTRY, ORGANIC rank: 44 / 52 = 0.846 (2022) - Q4 - T3
Factor impacto CITESCORE: 1.0 - Chemistry (Q4)
Factor impacto SCIMAGO: 0.182 - Organic Chemistry (Q4)
Financiación: info:eu-repo/grantAgreement/ES/AEI-MINECO-FEDER/CTQ2016-76782-P
Financiación: info:eu-repo/grantAgreement/ES/AEI-MINECO-FEDER/CTQ2016-80375-P
Financiación: info:eu-repo/grantAgreement/ES/MICINN/RED2018-102387-T
Financiación: info:eu-repo/grantAgreement/ES/MINECO-AEI-FEDER/CTQ2017-82935-P
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/PID2019-104090RB-100
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/PID2019-107268GB-I00
Tipo y forma: Article (Published version)
Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes.
Exportado de SIDERAL (2024-03-18-15:59:56)
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Idioma: Inglés
DOI: 10.24820/ark.5550190.p011.804
Año: 2022
Publicado en: ARKIVOC 2023, 3 (2022), 16-32
ISSN: 1551-7004
Factor impacto JCR: 0.9 (2022)
Categ. JCR: CHEMISTRY, ORGANIC rank: 44 / 52 = 0.846 (2022) - Q4 - T3
Factor impacto CITESCORE: 1.0 - Chemistry (Q4)
Factor impacto SCIMAGO: 0.182 - Organic Chemistry (Q4)
Financiación: info:eu-repo/grantAgreement/ES/AEI-MINECO-FEDER/CTQ2016-76782-P
Financiación: info:eu-repo/grantAgreement/ES/AEI-MINECO-FEDER/CTQ2016-80375-P
Financiación: info:eu-repo/grantAgreement/ES/MICINN/RED2018-102387-T
Financiación: info:eu-repo/grantAgreement/ES/MINECO-AEI-FEDER/CTQ2017-82935-P
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/PID2019-104090RB-100
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/PID2019-107268GB-I00
Tipo y forma: Article (Published version)
Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes. Exportado de SIDERAL (2024-03-18-15:59:56)
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Record created 2023-01-26, last modified 2024-03-19