Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester

An aryl substrate with dual functionality consisting of a nitrile oxide and a pinacolyl boronate ester was prepared by mild hypervalent iodine oxidation (diacetoxyiodobenzene) of the corresponding aldoxime, without decomposition of the boronate functionality. The nitrile oxide was trapped in situ wi...

Descripción completa

Detalles Bibliográficos
Autores principales: Harding, Sarah L, Marcuccio, Sebastian M, Savage, G Paul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3343286/
https://www.ncbi.nlm.nih.gov/pubmed/22563358
http://dx.doi.org/10.3762/bjoc.8.67
_version_ 1782231800297291776
author Harding, Sarah L
Marcuccio, Sebastian M
Savage, G Paul
author_facet Harding, Sarah L
Marcuccio, Sebastian M
Savage, G Paul
author_sort Harding, Sarah L
collection PubMed
description An aryl substrate with dual functionality consisting of a nitrile oxide and a pinacolyl boronate ester was prepared by mild hypervalent iodine oxidation (diacetoxyiodobenzene) of the corresponding aldoxime, without decomposition of the boronate functionality. The nitrile oxide was trapped in situ with a variety of dipolarophiles to yield aryl isoxazolines with the boronate ester function intact and available for subsequent reaction.
format Online
Article
Text
id pubmed-3343286
institution National Center for Biotechnology Information
language English
publishDate 2012
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-33432862012-05-04 Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester Harding, Sarah L Marcuccio, Sebastian M Savage, G Paul Beilstein J Org Chem Full Research Paper An aryl substrate with dual functionality consisting of a nitrile oxide and a pinacolyl boronate ester was prepared by mild hypervalent iodine oxidation (diacetoxyiodobenzene) of the corresponding aldoxime, without decomposition of the boronate functionality. The nitrile oxide was trapped in situ with a variety of dipolarophiles to yield aryl isoxazolines with the boronate ester function intact and available for subsequent reaction. Beilstein-Institut 2012-04-19 /pmc/articles/PMC3343286/ /pubmed/22563358 http://dx.doi.org/10.3762/bjoc.8.67 Text en Copyright © 2012, Harding 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
Harding, Sarah L
Marcuccio, Sebastian M
Savage, G Paul
Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester
title Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester
title_full Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester
title_fullStr Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester
title_full_unstemmed Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester
title_short Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester
title_sort aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3343286/
https://www.ncbi.nlm.nih.gov/pubmed/22563358
http://dx.doi.org/10.3762/bjoc.8.67
work_keys_str_mv AT hardingsarahl arylnitrileoxidecycloadditionreactionsinthepresenceofpinacolboronicacidester
AT marcucciosebastianm arylnitrileoxidecycloadditionreactionsinthepresenceofpinacolboronicacidester
AT savagegpaul arylnitrileoxidecycloadditionreactionsinthepresenceofpinacolboronicacidester

Ejemplares similares