Diastereoselective deacylative aldol reaction of 3-acetyl-3-fluorooxindoles with aldehydes

Autor: Inmaculada Sempere, Cynthia Molina, Eduardo García-Mingüens, Mª de Gracia Retamosa, Carmen Nájera, Pedro Merino, Miguel Yus, José M. Sansano
Rok vydání: 2022
Předmět:
Zdroj: Arkivoc. 2023:16-32
ISSN: 1551-7012
DOI: 10.24820/ark.5550190.p011.804
Popis: 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.
Databáze: OpenAIRE