Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters

Detailed investigations concerning the organocatalytic (asymmetric) α-azidation of prochiral β-ketoesters were carried out. It was shown that the racemic version of such a reaction can either be carried out under oxidative conditions using TMSN(3) as the azide-source with quaternary ammonium iodides...

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Autores principales: Tiffner, Maximilian, Stockhammer, Lotte, Schörgenhumer, Johannes, Röser, Katharina, Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6100502/
https://www.ncbi.nlm.nih.gov/pubmed/29751597
http://dx.doi.org/10.3390/molecules23051142
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author Tiffner, Maximilian
Stockhammer, Lotte
Schörgenhumer, Johannes
Röser, Katharina
Waser, Mario
author_facet Tiffner, Maximilian
Stockhammer, Lotte
Schörgenhumer, Johannes
Röser, Katharina
Waser, Mario
author_sort Tiffner, Maximilian
collection PubMed
description Detailed investigations concerning the organocatalytic (asymmetric) α-azidation of prochiral β-ketoesters were carried out. It was shown that the racemic version of such a reaction can either be carried out under oxidative conditions using TMSN(3) as the azide-source with quaternary ammonium iodides as the catalysts, or by using hypervalent iodine-based electrophilic azide-transfer reagents with different organocatalysts. In addition, the latter strategy could also be carried out with modest enantioselectivities when using simple cinchona alkaloid catalysts, albeit with relatively low yields.
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spelling pubmed-61005022018-11-13 Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters Tiffner, Maximilian Stockhammer, Lotte Schörgenhumer, Johannes Röser, Katharina Waser, Mario Molecules Article Detailed investigations concerning the organocatalytic (asymmetric) α-azidation of prochiral β-ketoesters were carried out. It was shown that the racemic version of such a reaction can either be carried out under oxidative conditions using TMSN(3) as the azide-source with quaternary ammonium iodides as the catalysts, or by using hypervalent iodine-based electrophilic azide-transfer reagents with different organocatalysts. In addition, the latter strategy could also be carried out with modest enantioselectivities when using simple cinchona alkaloid catalysts, albeit with relatively low yields. MDPI 2018-05-11 /pmc/articles/PMC6100502/ /pubmed/29751597 http://dx.doi.org/10.3390/molecules23051142 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tiffner, Maximilian
Stockhammer, Lotte
Schörgenhumer, Johannes
Röser, Katharina
Waser, Mario
Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters
title Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters
title_full Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters
title_fullStr Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters
title_full_unstemmed Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters
title_short Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters
title_sort towards an asymmetric organocatalytic α-azidation of β-ketoesters
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6100502/
https://www.ncbi.nlm.nih.gov/pubmed/29751597
http://dx.doi.org/10.3390/molecules23051142
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