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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...

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Autores principales: Zhu, Shaolin, Buchwald, Stephen L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
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.
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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
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