Highly enantioselective metallation–substitution alpha to a chiral nitrile

We report the deprotonation of a chiral nitrile and reaction of the resulting chiral organometallic species with a variety of electrophiles to give highly enantiomerically enriched 2-substituted nitrile products. The nitrile was treated with TMPMgCl and the resulting anion, an asymmetric alpha cyano...

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Autores principales: Sadhukhan, Arghya, Hobbs, Melanie C., Meijer, Anthony J. H. M., Coldham, Iain
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5460602/
https://www.ncbi.nlm.nih.gov/pubmed/28616143
http://dx.doi.org/10.1039/c6sc03712g
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author Sadhukhan, Arghya
Hobbs, Melanie C.
Meijer, Anthony J. H. M.
Coldham, Iain
author_facet Sadhukhan, Arghya
Hobbs, Melanie C.
Meijer, Anthony J. H. M.
Coldham, Iain
author_sort Sadhukhan, Arghya
collection PubMed
description We report the deprotonation of a chiral nitrile and reaction of the resulting chiral organometallic species with a variety of electrophiles to give highly enantiomerically enriched 2-substituted nitrile products. The nitrile was treated with TMPMgCl and the resulting anion, an asymmetric alpha cyano Grignard species, was found to be configurationally stable at low temperature for a short time (half-life several minutes at –104 °C).
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spelling pubmed-54606022017-06-14 Highly enantioselective metallation–substitution alpha to a chiral nitrile Sadhukhan, Arghya Hobbs, Melanie C. Meijer, Anthony J. H. M. Coldham, Iain Chem Sci Chemistry We report the deprotonation of a chiral nitrile and reaction of the resulting chiral organometallic species with a variety of electrophiles to give highly enantiomerically enriched 2-substituted nitrile products. The nitrile was treated with TMPMgCl and the resulting anion, an asymmetric alpha cyano Grignard species, was found to be configurationally stable at low temperature for a short time (half-life several minutes at –104 °C). Royal Society of Chemistry 2017-02-01 2016-10-25 /pmc/articles/PMC5460602/ /pubmed/28616143 http://dx.doi.org/10.1039/c6sc03712g Text en This journal is © The Royal Society of Chemistry 2016 https://creativecommons.org/licenses/by/3.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/ (https://creativecommons.org/licenses/by/3.0/) ) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Sadhukhan, Arghya
Hobbs, Melanie C.
Meijer, Anthony J. H. M.
Coldham, Iain
Highly enantioselective metallation–substitution alpha to a chiral nitrile
title Highly enantioselective metallation–substitution alpha to a chiral nitrile
title_full Highly enantioselective metallation–substitution alpha to a chiral nitrile
title_fullStr Highly enantioselective metallation–substitution alpha to a chiral nitrile
title_full_unstemmed Highly enantioselective metallation–substitution alpha to a chiral nitrile
title_short Highly enantioselective metallation–substitution alpha to a chiral nitrile
title_sort highly enantioselective metallation–substitution alpha to a chiral nitrile
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5460602/
https://www.ncbi.nlm.nih.gov/pubmed/28616143
http://dx.doi.org/10.1039/c6sc03712g
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AT hobbsmelaniec highlyenantioselectivemetallationsubstitutionalphatoachiralnitrile
AT meijeranthonyjhm highlyenantioselectivemetallationsubstitutionalphatoachiralnitrile
AT coldhamiain highlyenantioselectivemetallationsubstitutionalphatoachiralnitrile

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