N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines

Transition metal-mediated N–O bond cleavage reactions of heterobicycloalkene-fused 3-methyl-2-isoxazolines were investigated. Optimal cleavage conditions were found with Raney nickel/AlCl(3) mediation in aqueous methanol. The reaction provided a diverse collection of novel heterobicycle-fused β-hydr...

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Autores principales: Nagireddy, Jaipal R, Tranmer, Geoffrey K, Carlson, Emily, Tam, William
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168885/
https://www.ncbi.nlm.nih.gov/pubmed/25246978
http://dx.doi.org/10.3762/bjoc.10.227
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author Nagireddy, Jaipal R
Tranmer, Geoffrey K
Carlson, Emily
Tam, William
author_facet Nagireddy, Jaipal R
Tranmer, Geoffrey K
Carlson, Emily
Tam, William
author_sort Nagireddy, Jaipal R
collection PubMed
description Transition metal-mediated N–O bond cleavage reactions of heterobicycloalkene-fused 3-methyl-2-isoxazolines were investigated. Optimal cleavage conditions were found with Raney nickel/AlCl(3) mediation in aqueous methanol. The reaction provided a diverse collection of novel heterobicycle-fused β-hydroxyketones with good to excellent yields (66–95%) and without the need for chromatographic purification.
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spelling pubmed-41688852014-09-22 N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines Nagireddy, Jaipal R Tranmer, Geoffrey K Carlson, Emily Tam, William Beilstein J Org Chem Full Research Paper Transition metal-mediated N–O bond cleavage reactions of heterobicycloalkene-fused 3-methyl-2-isoxazolines were investigated. Optimal cleavage conditions were found with Raney nickel/AlCl(3) mediation in aqueous methanol. The reaction provided a diverse collection of novel heterobicycle-fused β-hydroxyketones with good to excellent yields (66–95%) and without the need for chromatographic purification. Beilstein-Institut 2014-09-16 /pmc/articles/PMC4168885/ /pubmed/25246978 http://dx.doi.org/10.3762/bjoc.10.227 Text en Copyright © 2014, Nagireddy et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Nagireddy, Jaipal R
Tranmer, Geoffrey K
Carlson, Emily
Tam, William
N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
title N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
title_full N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
title_fullStr N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
title_full_unstemmed N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
title_short N–O Cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
title_sort n–o cleavage reactions of heterobicycloalkene-fused 2-isoxazolines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168885/
https://www.ncbi.nlm.nih.gov/pubmed/25246978
http://dx.doi.org/10.3762/bjoc.10.227
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