Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium(I) Migration

Alkenyl‐to‐allyl 1,4‐rhodium(I) migration enables the generation of nucleophilic allylrhodium(I) species by remote C−H activation. This new mode of reactivity was employed in the diastereoselective reaction of arylboron reagents with substrates containing a 1,3‐enyne tethered to a ketone, to give pr...

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Detalles Bibliográficos
Autores principales: Partridge, Benjamin M., Callingham, Michael, Lewis, William, Lam, Hon Wai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5488243/
https://www.ncbi.nlm.nih.gov/pubmed/28523779
http://dx.doi.org/10.1002/anie.201703155
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author Partridge, Benjamin M.
Callingham, Michael
Lewis, William
Lam, Hon Wai
author_facet Partridge, Benjamin M.
Callingham, Michael
Lewis, William
Lam, Hon Wai
author_sort Partridge, Benjamin M.
collection PubMed
description Alkenyl‐to‐allyl 1,4‐rhodium(I) migration enables the generation of nucleophilic allylrhodium(I) species by remote C−H activation. This new mode of reactivity was employed in the diastereoselective reaction of arylboron reagents with substrates containing a 1,3‐enyne tethered to a ketone, to give products containing three contiguous stereocenters. The products can be obtained in high enantioselectivities using a chiral sulfur‐alkene ligand.
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spelling pubmed-54882432017-07-21 Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium(I) Migration Partridge, Benjamin M. Callingham, Michael Lewis, William Lam, Hon Wai Angew Chem Int Ed Engl Communications Alkenyl‐to‐allyl 1,4‐rhodium(I) migration enables the generation of nucleophilic allylrhodium(I) species by remote C−H activation. This new mode of reactivity was employed in the diastereoselective reaction of arylboron reagents with substrates containing a 1,3‐enyne tethered to a ketone, to give products containing three contiguous stereocenters. The products can be obtained in high enantioselectivities using a chiral sulfur‐alkene ligand. John Wiley and Sons Inc. 2017-05-19 2017-06-12 /pmc/articles/PMC5488243/ /pubmed/28523779 http://dx.doi.org/10.1002/anie.201703155 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
Partridge, Benjamin M.
Callingham, Michael
Lewis, William
Lam, Hon Wai
Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium(I) Migration
title Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium(I) Migration
title_full Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium(I) Migration
title_fullStr Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium(I) Migration
title_full_unstemmed Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium(I) Migration
title_short Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium(I) Migration
title_sort arylative intramolecular allylation of ketones with 1,3‐enynes enabled by catalytic alkenyl‐to‐allyl 1,4‐rhodium(i) migration
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5488243/
https://www.ncbi.nlm.nih.gov/pubmed/28523779
http://dx.doi.org/10.1002/anie.201703155
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