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Synfacts 2013; 9(1): 0084
DOI: 10.1055/s-0032-1317732
DOI: 10.1055/s-0032-1317732
Metal-Mediated Synthesis
Preparation and Rearrangement of N‑Vinyl Nitrones
Further Information
Publication History
Publication Date:
17 December 2012 (online)

Significance
Herein, the authors disclose the single-step, copper-mediated coupling of fluorene oximes and vinyl boronic acids, which undergo thermal rearrangement via [3+2] cycloaddition to form spiroisoxazolines. The corresponding N-vinyl nitrones and spiroisoxazolines are obtained in good yield.
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Comment
In addition, this methodology may be applied to the synthesis of fluorene-tethered isoxazoles by treatment of N-vinyl nitrones with terminal or internal electron-deficient alkynes. The mechanism is supposed to proceed via [3+2] cycloaddition and subsequent elimination.
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