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Synfacts 2013; 9(1): 0084
DOI: 10.1055/s-0032-1317732
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Preparation and Rearrangement of N‑Vinyl Nitrones

Contributor(s):
Paul Knochel
,
Nadja M. Barl
Mo D.-L, Wink DA, Anderson LL * University of Illinois at Chicago, USA
Preparation and Rearrangement of N-Vinyl Nitrones: Synthesis of Spiroisoxazolines and Fluorene-Tethered Isoxazoles.

Org. Lett. 2012;
14: 5180-5183
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

boron - copper - fluorenone oxime - N-vinyl nitrones - [3+2] cycloaddition

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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