Copper‐Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β‐and γ‐Amino­alkyl)boronic Esters

Cyclic sulfamidates undergo borylation under copper‐catalyzed conditions using B(2)pin(2) to give enantiomerically (and diasteromerically) defined (aminoalkyl)boronic esters. External iodide is essential, but the intermediacy of simple alkyl iodides has been excluded; N‐sulfated intermediates are ke...

Descripción completa

Detalles Bibliográficos
Autores principales: Ursinyova, Nina, Bedford, Robin B., Gallagher, Timothy
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY‐VCH Verlag 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4770434/
http://dx.doi.org/10.1002/ejoc.201501492
_version_ 1782418266243727360
author Ursinyova, Nina
Bedford, Robin B.
Gallagher, Timothy
author_facet Ursinyova, Nina
Bedford, Robin B.
Gallagher, Timothy
author_sort Ursinyova, Nina
collection PubMed
description Cyclic sulfamidates undergo borylation under copper‐catalyzed conditions using B(2)pin(2) to give enantiomerically (and diasteromerically) defined (aminoalkyl)boronic esters. External iodide is essential, but the intermediacy of simple alkyl iodides has been excluded; N‐sulfated intermediates are key in the borylation sequence. Based on stereochemical studies and trapping experiments, the involvement of carbon‐centered radicals under these copper‐catalyzed conditions appears likely.
format Online
Article
Text
id pubmed-4770434
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher WILEY‐VCH Verlag
record_format MEDLINE/PubMed
spelling pubmed-47704342016-04-11 Copper‐Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β‐and γ‐Amino­alkyl)boronic Esters Ursinyova, Nina Bedford, Robin B. Gallagher, Timothy European J Org Chem Communications Cyclic sulfamidates undergo borylation under copper‐catalyzed conditions using B(2)pin(2) to give enantiomerically (and diasteromerically) defined (aminoalkyl)boronic esters. External iodide is essential, but the intermediacy of simple alkyl iodides has been excluded; N‐sulfated intermediates are key in the borylation sequence. Based on stereochemical studies and trapping experiments, the involvement of carbon‐centered radicals under these copper‐catalyzed conditions appears likely. WILEY‐VCH Verlag 2015-12-23 2016-02 /pmc/articles/PMC4770434/ http://dx.doi.org/10.1002/ejoc.201501492 Text en © 2016 The Authors. Published by WILEY‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. Open access.
spellingShingle Communications
Ursinyova, Nina
Bedford, Robin B.
Gallagher, Timothy
Copper‐Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β‐and γ‐Amino­alkyl)boronic Esters
title Copper‐Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β‐and γ‐Amino­alkyl)boronic Esters
title_full Copper‐Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β‐and γ‐Amino­alkyl)boronic Esters
title_fullStr Copper‐Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β‐and γ‐Amino­alkyl)boronic Esters
title_full_unstemmed Copper‐Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β‐and γ‐Amino­alkyl)boronic Esters
title_short Copper‐Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β‐and γ‐Amino­alkyl)boronic Esters
title_sort copper‐catalyzed borylation of cyclic sulfamidates: access to enantiomerically pure (β‐and γ‐amino­alkyl)boronic esters
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4770434/
http://dx.doi.org/10.1002/ejoc.201501492
work_keys_str_mv AT ursinyovanina coppercatalyzedborylationofcyclicsulfamidatesaccesstoenantiomericallypurebandgaminoalkylboronicesters
AT bedfordrobinb coppercatalyzedborylationofcyclicsulfamidatesaccesstoenantiomericallypurebandgaminoalkylboronicesters
AT gallaghertimothy coppercatalyzedborylationofcyclicsulfamidatesaccesstoenantiomericallypurebandgaminoalkylboronicesters

Ejemplares similares