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Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes
[Image: see text] Enantioselective synthesis of β-chiral amines has been achieved via copper-catalyzed hydroamination of 1,1-disubstituted alkenes with hydroxylamine esters in the presence of a hydrosilane. This mild process affords a range of structurally diverse β-chiral amines, including β-deuter...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2014
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4235366/ https://www.ncbi.nlm.nih.gov/pubmed/25339089 http://dx.doi.org/10.1021/ja509786v |
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author | Zhu, Shaolin Buchwald, Stephen L. |
author_facet | Zhu, Shaolin Buchwald, Stephen L. |
author_sort | Zhu, Shaolin |
collection | PubMed |
description | [Image: see text] Enantioselective synthesis of β-chiral amines has been achieved via copper-catalyzed hydroamination of 1,1-disubstituted alkenes with hydroxylamine esters in the presence of a hydrosilane. This mild process affords a range of structurally diverse β-chiral amines, including β-deuterated amines, in excellent yields with high enantioselectivities. Furthermore, catalyst loading as low as 0.4 mol% could be employed to deliver product in undiminished yield and selectivity, demonstrating the practicality of this method for large-scale synthesis. |
format | Online Article Text |
id | pubmed-4235366 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-42353662015-10-22 Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes Zhu, Shaolin Buchwald, Stephen L. J Am Chem Soc [Image: see text] Enantioselective synthesis of β-chiral amines has been achieved via copper-catalyzed hydroamination of 1,1-disubstituted alkenes with hydroxylamine esters in the presence of a hydrosilane. This mild process affords a range of structurally diverse β-chiral amines, including β-deuterated amines, in excellent yields with high enantioselectivities. Furthermore, catalyst loading as low as 0.4 mol% could be employed to deliver product in undiminished yield and selectivity, demonstrating the practicality of this method for large-scale synthesis. American Chemical Society 2014-10-22 2014-11-12 /pmc/articles/PMC4235366/ /pubmed/25339089 http://dx.doi.org/10.1021/ja509786v Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Zhu, Shaolin Buchwald, Stephen L. Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes |
title | Enantioselective
CuH-Catalyzed Anti-Markovnikov Hydroamination
of 1,1-Disubstituted Alkenes |
title_full | Enantioselective
CuH-Catalyzed Anti-Markovnikov Hydroamination
of 1,1-Disubstituted Alkenes |
title_fullStr | Enantioselective
CuH-Catalyzed Anti-Markovnikov Hydroamination
of 1,1-Disubstituted Alkenes |
title_full_unstemmed | Enantioselective
CuH-Catalyzed Anti-Markovnikov Hydroamination
of 1,1-Disubstituted Alkenes |
title_short | Enantioselective
CuH-Catalyzed Anti-Markovnikov Hydroamination
of 1,1-Disubstituted Alkenes |
title_sort | enantioselective
cuh-catalyzed anti-markovnikov hydroamination
of 1,1-disubstituted alkenes |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4235366/ https://www.ncbi.nlm.nih.gov/pubmed/25339089 http://dx.doi.org/10.1021/ja509786v |
work_keys_str_mv | AT zhushaolin enantioselectivecuhcatalyzedantimarkovnikovhydroaminationof11disubstitutedalkenes AT buchwaldstephenl enantioselectivecuhcatalyzedantimarkovnikovhydroaminationof11disubstitutedalkenes |