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 in situ ketonitrone from unsaturated ketones and N-alkylhydroxylamines is...

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Detalles Bibliográficos
Autores principales: Liu, Yilin, Liu, Jiaxue, Liu, Yan-Yun, Tang, Boxiao, Lin, Hongwei, Li, Yuanxiang, Zhang, Lin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9041119/
https://www.ncbi.nlm.nih.gov/pubmed/35480251
http://dx.doi.org/10.1039/d1ra06063e
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author Liu, Yilin
Liu, Jiaxue
Liu, Yan-Yun
Tang, Boxiao
Lin, Hongwei
Li, Yuanxiang
Zhang, Lin
author_facet Liu, Yilin
Liu, Jiaxue
Liu, Yan-Yun
Tang, Boxiao
Lin, Hongwei
Li, Yuanxiang
Zhang, Lin
author_sort Liu, Yilin
collection PubMed
description 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 in situ ketonitrone from unsaturated ketones and N-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.
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spelling pubmed-90411192022-04-26 Synthesis of spirocyclic Δ(4)-isoxazolines via [3 + 2] cycloaddition of indanone-derived ketonitrones with alkynes Liu, Yilin Liu, Jiaxue Liu, Yan-Yun Tang, Boxiao Lin, Hongwei Li, Yuanxiang Zhang, Lin RSC Adv Chemistry 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 in situ ketonitrone from unsaturated ketones and N-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. The Royal Society of Chemistry 2021-09-13 /pmc/articles/PMC9041119/ /pubmed/35480251 http://dx.doi.org/10.1039/d1ra06063e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Liu, Yilin
Liu, Jiaxue
Liu, Yan-Yun
Tang, Boxiao
Lin, Hongwei
Li, Yuanxiang
Zhang, Lin
Synthesis of spirocyclic Δ(4)-isoxazolines via [3 + 2] cycloaddition of indanone-derived ketonitrones with alkynes
title Synthesis of spirocyclic Δ(4)-isoxazolines via [3 + 2] cycloaddition of indanone-derived ketonitrones with alkynes
title_full Synthesis of spirocyclic Δ(4)-isoxazolines via [3 + 2] cycloaddition of indanone-derived ketonitrones with alkynes
title_fullStr Synthesis of spirocyclic Δ(4)-isoxazolines via [3 + 2] cycloaddition of indanone-derived ketonitrones with alkynes
title_full_unstemmed Synthesis of spirocyclic Δ(4)-isoxazolines via [3 + 2] cycloaddition of indanone-derived ketonitrones with alkynes
title_short Synthesis of spirocyclic Δ(4)-isoxazolines via [3 + 2] cycloaddition of indanone-derived ketonitrones with alkynes
title_sort synthesis of spirocyclic δ(4)-isoxazolines via [3 + 2] cycloaddition of indanone-derived ketonitrones with alkynes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9041119/
https://www.ncbi.nlm.nih.gov/pubmed/35480251
http://dx.doi.org/10.1039/d1ra06063e
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