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2025-05-27

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cc-by (c) Balaguer Garcia, Eduard et al., 2025
Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/221878

In search of radical transformations from metal enolates. Direct reactions of N‑acyl-1,3-oxazolidin-2-ones with TEMPO catalyzed by copper(II) acetate

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https://doi.org/10.1021/acs.joc.5c00457

Abstract

The direct reactions of a diverse range of N-acyl-1,3-oxazolidin-2-ones with TEMPO, catalyzed by copper(II) acetate and 4,7-dimethyl-1,10-phenanthroline without the need for any base, are herein described. These reactions afford the corresponding aminoxylated derivatives with high chemoselectivity and complete regioselectivity, achieving excellent yields under mild conditions. Further treatment of the resulting imides enables access to a variety of formally protected hydroxy compounds, which can be regarded as valuable synthetic intermediates. The efficient formal synthesis of isoproterenol highlights the potential of this methodology and sets the stage for further advancements in the catalytic chemistry of metal enolates.

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Alcohols, Compostos orgànics, Metalls

Subject (English)

Alcohols, Organic compounds, Metals

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Articles publicats en revistes (Química Inorgànica i Orgànica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

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BALAGUER GARCIA, Eduard, et al. In search of radical transformations from metal enolates. Direct reactions of N‑acyl-1,3-oxazolidin-2-ones with TEMPO catalyzed by copper(II) acetate. Journal of Organic Chemistry. 2025. Vol. 90, num. 7332-7339. ISSN 0022-3263. [consulted: 9 of August of 2026]. Available at: https://hdl.handle.net/2445/221878

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