Electroreductive Ring-Opening Carboxylation of 1,3-Oxazolidin-2-ones with CO2 for Accessing β‑Amino Acids

Electrocarboxylation of the C­(sp3)–O bond in 1,3-oxazolidin-2-ones with CO2 to achieve β-amino acids is developed. The C–O bond in substrates can be selectively cleaved via the single electron transfer on the surface of a cathode or through a CO2 • – intermediate under additive-free conditions. A g...

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Veröffentlicht in:Organic letters 2024-01, Vol.26 (2), p.542-546
Hauptverfasser: Tao, Li, Liu, Xiao-Fei, Ren, Bai-Hao, Wang, He, Sun, Hui-Qin, Zhang, Ke, Teng, Yong-Qiang, Ren, Wei-Min, Lu, Xiao-Bing, Zhang, Wen-Zhen
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Sprache:eng
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Zusammenfassung:Electrocarboxylation of the C­(sp3)–O bond in 1,3-oxazolidin-2-ones with CO2 to achieve β-amino acids is developed. The C–O bond in substrates can be selectively cleaved via the single electron transfer on the surface of a cathode or through a CO2 • – intermediate under additive-free conditions. A great diversity of β-amino acids can be obtained in a moderate to excellent yield and readily converted to various biologically active compounds.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c04007