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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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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. |
format | Online Article Text |
id | pubmed-8790592 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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