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Mo DL, Wink DA, Anderson LL. Preparation and rearrangement of N-vinyl nitrones: synthesis of spiroisoxazolines and fluorene-tethered isoxazoles. Org Lett. 2012;14(20):5180-3doi: 10.1021/ol3022885.
Mo, D. L., Wink, D. A., & Anderson, L. L. (2012). Preparation and rearrangement of N-vinyl nitrones: synthesis of spiroisoxazolines and fluorene-tethered isoxazoles. Organic letters, 14(20), 5180-3. https://doi.org/10.1021/ol3022885
Mo, Dong-Liang, et al. "Preparation and rearrangement of N-vinyl nitrones: synthesis of spiroisoxazolines and fluorene-tethered isoxazoles." Organic letters vol. 14,20 (2012): 5180-3. doi: https://doi.org/10.1021/ol3022885
Mo DL, Wink DA, Anderson LL. Preparation and rearrangement of N-vinyl nitrones: synthesis of spiroisoxazolines and fluorene-tethered isoxazoles. Org Lett. 2012 Oct 19;14(20):5180-3. doi: 10.1021/ol3022885. Epub 2012 Oct 09. PMID: 23046082.
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Org Lett. 2012 Oct 19;14(20):5180-3. doi: 10.1021/ol3022885. Epub 2012 Oct 09.

Preparation and rearrangement of N-vinyl nitrones: synthesis of spiroisoxazolines and fluorene-tethered isoxazoles.

Organic letters

Dong-Liang Mo, Donald A Wink, Laura L Anderson

Affiliations

  1. University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA.

PMID: 23046082 DOI: 10.1021/ol3022885

Abstract

N-Vinyl nitrones derived from fluorenone have been prepared via a copper-mediated coupling between fluorenone oxime and vinyl boronic acids. These compounds undergo subsequent rearrangement and addition reactions that are distinct from the traditional [3 + 2] cycloaddition reactivity of nitrones. Thermal rearrangements of fluorenone N-vinyl nitrones give spiroisoxazolines, while treatment with alkynes provides fluorene-tethered isoxazoles. The scope and limitations of the preparation of fluorenone N-vinyl nitrones and their subsequent rearrangement and addition reactions are discussed.

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