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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...

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Detalles Bibliográficos
Autores principales: Harding, Sarah L, Marcuccio, Sebastian M, Savage, G Paul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
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
Descripción
Sumario: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.