A straightforward approach towards combined α-amino and α-hydroxy acids based on Passerini reactions

Complex amino acids with an α-acyloxycarbonyl functionality in the side chain are easily available through epoxide opening by chelated enolates and subsequent oxidation/Passerini reaction. This protocol works with both, aldehyde and ketone intermediates, as long as the ketones are activated by elect...

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Detalles Bibliográficos
Autores principales: Zahoor, Ameer F, Thies, Sarah, Kazmaier, Uli
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3182440/
https://www.ncbi.nlm.nih.gov/pubmed/21977215
http://dx.doi.org/10.3762/bjoc.7.151
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author Zahoor, Ameer F
Thies, Sarah
Kazmaier, Uli
author_facet Zahoor, Ameer F
Thies, Sarah
Kazmaier, Uli
author_sort Zahoor, Ameer F
collection PubMed
description Complex amino acids with an α-acyloxycarbonyl functionality in the side chain are easily available through epoxide opening by chelated enolates and subsequent oxidation/Passerini reaction. This protocol works with both, aldehyde and ketone intermediates, as long as the ketones are activated by electron-withdrawing groups. In principle Ugi reactions are also possible, allowing the generation of diamino acid derivatives.
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spelling pubmed-31824402011-10-05 A straightforward approach towards combined α-amino and α-hydroxy acids based on Passerini reactions Zahoor, Ameer F Thies, Sarah Kazmaier, Uli Beilstein J Org Chem Full Research Paper Complex amino acids with an α-acyloxycarbonyl functionality in the side chain are easily available through epoxide opening by chelated enolates and subsequent oxidation/Passerini reaction. This protocol works with both, aldehyde and ketone intermediates, as long as the ketones are activated by electron-withdrawing groups. In principle Ugi reactions are also possible, allowing the generation of diamino acid derivatives. Beilstein-Institut 2011-09-19 /pmc/articles/PMC3182440/ /pubmed/21977215 http://dx.doi.org/10.3762/bjoc.7.151 Text en Copyright © 2011, Zahoor et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Zahoor, Ameer F
Thies, Sarah
Kazmaier, Uli
A straightforward approach towards combined α-amino and α-hydroxy acids based on Passerini reactions
title A straightforward approach towards combined α-amino and α-hydroxy acids based on Passerini reactions
title_full A straightforward approach towards combined α-amino and α-hydroxy acids based on Passerini reactions
title_fullStr A straightforward approach towards combined α-amino and α-hydroxy acids based on Passerini reactions
title_full_unstemmed A straightforward approach towards combined α-amino and α-hydroxy acids based on Passerini reactions
title_short A straightforward approach towards combined α-amino and α-hydroxy acids based on Passerini reactions
title_sort straightforward approach towards combined α-amino and α-hydroxy acids based on passerini reactions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3182440/
https://www.ncbi.nlm.nih.gov/pubmed/21977215
http://dx.doi.org/10.3762/bjoc.7.151
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