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Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters
Herein, we report a Zn–ProPhenol catalyzed direct asymmetric amination reaction of unactivated aryl and vinyl ketones using di-tert-butyl azodicarboxylate as a cheap and practical electrophilic nitrogen source. Importantly, this methodology works with both α-branched and unbranched ketones for the c...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5897889/ https://www.ncbi.nlm.nih.gov/pubmed/29719678 http://dx.doi.org/10.1039/c8sc00147b |
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author | Trost, B. M. Tracy, J. S. Saget, T. |
author_facet | Trost, B. M. Tracy, J. S. Saget, T. |
author_sort | Trost, B. M. |
collection | PubMed |
description | Herein, we report a Zn–ProPhenol catalyzed direct asymmetric amination reaction of unactivated aryl and vinyl ketones using di-tert-butyl azodicarboxylate as a cheap and practical electrophilic nitrogen source. Importantly, this methodology works with both α-branched and unbranched ketones for the construction of tri- and tetrasubstituted N-containing stereocenters. The reaction can be run at gram-scale with low catalyst loadings and features a recoverable and reusable ligand. Finally, the enantioenriched hydrazine products can be readily converted into versatile building blocks such as α-amino carbonyl compounds and β-amino alcohols. |
format | Online Article Text |
id | pubmed-5897889 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-58978892018-05-01 Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters Trost, B. M. Tracy, J. S. Saget, T. Chem Sci Chemistry Herein, we report a Zn–ProPhenol catalyzed direct asymmetric amination reaction of unactivated aryl and vinyl ketones using di-tert-butyl azodicarboxylate as a cheap and practical electrophilic nitrogen source. Importantly, this methodology works with both α-branched and unbranched ketones for the construction of tri- and tetrasubstituted N-containing stereocenters. The reaction can be run at gram-scale with low catalyst loadings and features a recoverable and reusable ligand. Finally, the enantioenriched hydrazine products can be readily converted into versatile building blocks such as α-amino carbonyl compounds and β-amino alcohols. Royal Society of Chemistry 2018-02-14 /pmc/articles/PMC5897889/ /pubmed/29719678 http://dx.doi.org/10.1039/c8sc00147b Text en This journal is © The Royal Society of Chemistry 2018 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
spellingShingle | Chemistry Trost, B. M. Tracy, J. S. Saget, T. Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters |
title | Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters
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title_full | Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters
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title_fullStr | Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters
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title_full_unstemmed | Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters
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title_short | Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters
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title_sort | direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5897889/ https://www.ncbi.nlm.nih.gov/pubmed/29719678 http://dx.doi.org/10.1039/c8sc00147b |
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