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

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Title: Diastereoselective deacylative aldol reaction of 3-acetyl-3-fluorooxindoles with aldehydes
Authors: Sempere, Inmaculada | Molina, Cynthia | García-Mingüens, Eduardo | Retamosa, Maria de Gracia | Nájera, Carmen | Merino, Pedro | Yus, Miguel | Sansano, Jose M.
Research Group/s: Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Fluorine | Oxindole | Deacetylative | Aldol | Lewis acid | Syn-diastereoselectivity | DFT
Issue Date: 14-Aug-2022
Publisher: Arkat USA, Inc.
Citation: Arkivoc. 2022, part iii: 16-32. https://doi.org/10.24820/ark.5550190.p011.804
Abstract: 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.
Sponsor: We gratefully acknowledge financial support from the Spanish Ministerio de Ciencia, Innovación y Universidades (project RED2018-102387-T) the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P, CTQ2016-80375-P, CTQ2017-82935-P, PID2019-104090RB-100 and PID2019-107268GB-I00), the Generalitat Valenciana (IDIFEDER/2021/013, CIDEGENT/2020/058 and APOTIP/2020/002), Medalchemy S. L. (Medalchemy-18T) and the University of Alicante (VIGROB-068, UAUSTI21-05). P.M. thanks the Regional Government of Aragon (Grupos 17R-34 and a pre-doctoral contract to M.P.) for financial support. The authors thankfully acknowledge the resources from the super-computers "Memento" and “Cierzo”, technical expertise and assistance provided by BIFI-ZCAM (Universidad de Zaragoza, Spain).
URI: http://hdl.handle.net/10045/126917
ISSN: 1551-7004 (Print) | 1551-7012 (Online)
DOI: 10.24820/ark.5550190.p011.804
Language: eng
Type: info:eu-repo/semantics/article
Rights: © Author(s). This paper is an open access article distributed under the terms of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/)
Peer Review: si
Publisher version: https://doi.org/10.24820/ark.5550190.p011.804
Appears in Collections:INV - SINTAS - Artículos de Revistas

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