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)