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Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines

We have devised a highly regio- and enantioselective iridium-catalyzed allylic amination reaction with the sulfur-stabilized aza-ylide, S,S-diphenylsulfilimine. This process provides a robust and scalable method for the construction of aryl-, alkyl- and alkenyl-substituted C-chiral allylic sulfilimi...

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Autores principales: Grange, Rebecca L., Clizbe, Elizabeth A., Counsell, Emma J., Evans, P. Andrew
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5592745/
https://www.ncbi.nlm.nih.gov/pubmed/28936319
http://dx.doi.org/10.1039/c4sc01317d
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author Grange, Rebecca L.
Clizbe, Elizabeth A.
Counsell, Emma J.
Evans, P. Andrew
author_facet Grange, Rebecca L.
Clizbe, Elizabeth A.
Counsell, Emma J.
Evans, P. Andrew
author_sort Grange, Rebecca L.
collection PubMed
description We have devised a highly regio- and enantioselective iridium-catalyzed allylic amination reaction with the sulfur-stabilized aza-ylide, S,S-diphenylsulfilimine. This process provides a robust and scalable method for the construction of aryl-, alkyl- and alkenyl-substituted C-chiral allylic sulfilimines, which are important functional groups for organic synthesis. Additionally, the combination of the allylic amination with an in situ deprotection of the sulfilimine constitutes a convenient one-pot protocol for the construction of chiral nonracemic primary allylic amines.
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spelling pubmed-55927452017-09-21 Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines Grange, Rebecca L. Clizbe, Elizabeth A. Counsell, Emma J. Evans, P. Andrew Chem Sci Chemistry We have devised a highly regio- and enantioselective iridium-catalyzed allylic amination reaction with the sulfur-stabilized aza-ylide, S,S-diphenylsulfilimine. This process provides a robust and scalable method for the construction of aryl-, alkyl- and alkenyl-substituted C-chiral allylic sulfilimines, which are important functional groups for organic synthesis. Additionally, the combination of the allylic amination with an in situ deprotection of the sulfilimine constitutes a convenient one-pot protocol for the construction of chiral nonracemic primary allylic amines. Royal Society of Chemistry 2015-01-01 2014-09-08 /pmc/articles/PMC5592745/ /pubmed/28936319 http://dx.doi.org/10.1039/c4sc01317d Text en This journal is © The Royal Society of Chemistry 2014 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
Grange, Rebecca L.
Clizbe, Elizabeth A.
Counsell, Emma J.
Evans, P. Andrew
Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines
title Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines
title_full Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines
title_fullStr Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines
title_full_unstemmed Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines
title_short Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines
title_sort enantioselective construction of c-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with s,s-diphenylsulfilimine: asymmetric synthesis of primary allylic amines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5592745/
https://www.ncbi.nlm.nih.gov/pubmed/28936319
http://dx.doi.org/10.1039/c4sc01317d
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