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Enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives

Selenium-containing amino acids are valuable targets but methods for the stereoselective α-selenation of simple amino acid precursors are rare. We herein report the enantioselective electrophilic α-selenation of azlactones (masked α-amino acid derivatives) and isoxazolidin-5-ones (masked β-amino aci...

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Autores principales: Haider, Victoria, Zebrowski, Paul, Michalke, Jessica, Monkowius, Uwe, Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8790592/
https://www.ncbi.nlm.nih.gov/pubmed/35015015
http://dx.doi.org/10.1039/d1ob02235k
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author Haider, Victoria
Zebrowski, Paul
Michalke, Jessica
Monkowius, Uwe
Waser, Mario
author_facet Haider, Victoria
Zebrowski, Paul
Michalke, Jessica
Monkowius, Uwe
Waser, Mario
author_sort Haider, Victoria
collection PubMed
description Selenium-containing amino acids are valuable targets but methods for the stereoselective α-selenation of simple amino acid precursors are rare. We herein report the enantioselective electrophilic α-selenation of azlactones (masked α-amino acid derivatives) and isoxazolidin-5-ones (masked β-amino acids) using Cinchona alkaloids as easily accessible organocatalysts. A variety of differently substituted derivatives was accessed with reasonable levels of enantioselectivities and further studies concerning the stability and suitability of these compounds for further manipulations have been carried out as well.
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spelling pubmed-87905922022-02-23 Enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives Haider, Victoria Zebrowski, Paul Michalke, Jessica Monkowius, Uwe Waser, Mario Org Biomol Chem Chemistry Selenium-containing amino acids are valuable targets but methods for the stereoselective α-selenation of simple amino acid precursors are rare. We herein report the enantioselective electrophilic α-selenation of azlactones (masked α-amino acid derivatives) and isoxazolidin-5-ones (masked β-amino acids) using Cinchona alkaloids as easily accessible organocatalysts. A variety of differently substituted derivatives was accessed with reasonable levels of enantioselectivities and further studies concerning the stability and suitability of these compounds for further manipulations have been carried out as well. The Royal Society of Chemistry 2022-01-03 /pmc/articles/PMC8790592/ /pubmed/35015015 http://dx.doi.org/10.1039/d1ob02235k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Haider, Victoria
Zebrowski, Paul
Michalke, Jessica
Monkowius, Uwe
Waser, Mario
Enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives
title Enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives
title_full Enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives
title_fullStr Enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives
title_full_unstemmed Enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives
title_short Enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives
title_sort enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8790592/
https://www.ncbi.nlm.nih.gov/pubmed/35015015
http://dx.doi.org/10.1039/d1ob02235k
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