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DOI: 10.1055/a-2644-2389
Deacetylative Protocol to Obtain Diastereoselectively α-Fluoro-β-amino-oxindoles via a Mannich-Type Reaction using Aliphatic N-tert-Butanesulfinyl Imines
Authors
Supported by: University of Zaragoza, Spain
Supported by: Biological and Computational Research Group, University of Zaragoza, Spain
Supported by: The Ministerio de Ciencia e Innovación (Spain) E34_23R,PID2022-137973NB-100
Supported by: University of Alicante APOTIP/2021/020,CIAPOT/2022/11,COVID19/2021/079,IDIFEDER/2021/013,PID2019-107268GB-100,RED2018-102387-T,RED2022-134287-T
Supported by: VIGROB UADIF17-42,UAUSTI16-02,UAUSTI21-05
Funding Information The Ministerio de Ciencia e Innovación (Spain) (Project PID2022-137973NB-100) and the Government of Aragón (Spain) (Group of Reference, E34_23R) are acknowledged for financial support. We thank the Ministerio de Ciencia, Innovación y Universidades (RED2018-102387-T, RED2022-134287-T, and PID2019-107268GB-100) funded by MCIN/AEI/10.13039/501100011033 and Conselleria de Educación, Cultura, Universidades y Empleo (IDIFEDER/2021/013, GVA-COVID19/2021/079 CIAPOT/2022/11, and APOTIP/2021/020), the University of Alicante (VIGROB-050; UADIF17-42 UAUSTI16-02, VIGROB-068 and UAUSTI21-05) and Medalchemy S. L. (Medalchemy 22T).
Dedication
Dedicated to Professor Paul Knochel on the occasion of his 70th birthday.
Abstract
The deacetylative reaction of 3-acetyl-3-fluoro-2-oxindoles with a mild base promotes the in situ generation of 3-fluoro-2-oxindole enolates which react with aliphatic N-tert-butanesulfinyl imines via the Mannich-type reaction generating α-fluoro-β-sulfinylamino oxindoles in a diastereoselective way. The orientation of the attack of the enolate to the imine was computationally investigated, and the analysis of the absolute configuration of the resulting products was performed according to vibrational circular dichroism.
Publication History
Received: 07 April 2025
Accepted after revision: 26 June 2025
Article published online:
19 August 2025
© 2025. Thieme. All rights reserved.
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