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

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  • معلومة اضافية
    • Contributors:
      Universidad de Alicante. Departamento de Química Orgánica; Universidad de Alicante. Instituto Universitario de Síntesis Orgánica; Síntesis Asimétrica (SINTAS)
    • بيانات النشر:
      Arkat USA, Inc.
    • الموضوع:
      2022
    • Collection:
      RUA - Repositorio Institucional de la Universidad de Alicante
    • نبذة مختصرة :
      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. ; 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).
    • Relation:
      https://doi.org/10.24820/ark.5550190.p011.804; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RED2018-102387-T; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-76782-P; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-80375-P; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-82935-P; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-104090RB-I00; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-107268GB-I00; Arkivoc. 2022, part iii: 16-32. https://doi.org/10.24820/ark.5550190.p011.804; 1551-7004 (Print); 1551-7012 (Online); http://hdl.handle.net/10045/126917
    • الرقم المعرف:
      10.24820/ark.5550190.p011.804
    • الدخول الالكتروني :
      http://hdl.handle.net/10045/126917
      https://doi.org/10.24820/ark.5550190.p011.804
    • 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/) ; info:eu-repo/semantics/openAccess
    • الرقم المعرف:
      edsbas.5C975D36