Stereodivergent Olefination of Enantioenriched Boronic Esters

A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition‐metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination....

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Autores principales: Armstrong, Roly J., García‐Ruiz, Cristina, Myers, Eddie L., Aggarwal, Varinder K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5347846/
https://www.ncbi.nlm.nih.gov/pubmed/27958668
http://dx.doi.org/10.1002/anie.201610387
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author Armstrong, Roly J.
García‐Ruiz, Cristina
Myers, Eddie L.
Aggarwal, Varinder K.
author_facet Armstrong, Roly J.
García‐Ruiz, Cristina
Myers, Eddie L.
Aggarwal, Varinder K.
author_sort Armstrong, Roly J.
collection PubMed
description A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition‐metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner.
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spelling pubmed-53478462017-03-23 Stereodivergent Olefination of Enantioenriched Boronic Esters Armstrong, Roly J. García‐Ruiz, Cristina Myers, Eddie L. Aggarwal, Varinder K. Angew Chem Int Ed Engl Communications A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition‐metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner. John Wiley and Sons Inc. 2016-12-13 2017-01-16 /pmc/articles/PMC5347846/ /pubmed/27958668 http://dx.doi.org/10.1002/anie.201610387 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Armstrong, Roly J.
García‐Ruiz, Cristina
Myers, Eddie L.
Aggarwal, Varinder K.
Stereodivergent Olefination of Enantioenriched Boronic Esters
title Stereodivergent Olefination of Enantioenriched Boronic Esters
title_full Stereodivergent Olefination of Enantioenriched Boronic Esters
title_fullStr Stereodivergent Olefination of Enantioenriched Boronic Esters
title_full_unstemmed Stereodivergent Olefination of Enantioenriched Boronic Esters
title_short Stereodivergent Olefination of Enantioenriched Boronic Esters
title_sort stereodivergent olefination of enantioenriched boronic esters
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5347846/
https://www.ncbi.nlm.nih.gov/pubmed/27958668
http://dx.doi.org/10.1002/anie.201610387
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