Synthesis of spirocyclic Δ 4 -isoxazolines via [3 + 2] cycloaddition of indanone-derived ketonitrones with alkynes

A [3 + 2] cycloaddition of indanone-derived nitrones and alkynes under mild conditions is developed, allowing facile synthesis of spirocyclicindenyl isoxazolines with structural diversity. The sequential protocol of generated ketonitrone from unsaturated ketones and -alkylhydroxylamines is also achi...

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Bibliographic Details
Published in:RSC advances 2021-09, Vol.11 (48), p.30415-30425
Main Authors: Liu, Yilin, Liu, Jiaxue, Liu, Yan-Yun, Tang, Boxiao, Lin, Hongwei, Li, Yuanxiang, Zhang, Lin
Format: Article
Language:English
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Summary:A [3 + 2] cycloaddition of indanone-derived nitrones and alkynes under mild conditions is developed, allowing facile synthesis of spirocyclicindenyl isoxazolines with structural diversity. The sequential protocol of generated ketonitrone from unsaturated ketones and -alkylhydroxylamines is also achieved successfully, affording the desired products in considerable yield with moderate to good diastereoselectivity. Moreover, the spirocyclic product can be conveniently transformed into indenyl-based allylic alcohol and enamide.
ISSN:2046-2069
2046-2069
DOI:10.1039/D1RA06063E