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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Royal Society of Chemistry
2015
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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. |
format | Online Article Text |
id | pubmed-5592745 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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
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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
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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
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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
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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
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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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