Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction

In this manuscript, a novel, decarboxylative Michael reaction between α-substituted azlactones and chromone-3-carboxylic acids is described. The reaction proceeds in a sequence Michael addition followed by decarboxylative deprotonation, and it results in the formation of chromanones bearing an azlac...

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Autores principales: Bojanowski, Jan, Sieroń, Lesław, Albrecht, Anna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6681191/
https://www.ncbi.nlm.nih.gov/pubmed/31311096
http://dx.doi.org/10.3390/molecules24142565
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author Bojanowski, Jan
Sieroń, Lesław
Albrecht, Anna
author_facet Bojanowski, Jan
Sieroń, Lesław
Albrecht, Anna
author_sort Bojanowski, Jan
collection PubMed
description In this manuscript, a novel, decarboxylative Michael reaction between α-substituted azlactones and chromone-3-carboxylic acids is described. The reaction proceeds in a sequence Michael addition followed by decarboxylative deprotonation, and it results in the formation of chromanones bearing an azlactone structural unit. The possibility of transforming an azlactone moiety into a protected α,α-disubstituted α-amino acid derivative is also demonstrated.
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spelling pubmed-66811912019-08-09 Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction Bojanowski, Jan Sieroń, Lesław Albrecht, Anna Molecules Communication In this manuscript, a novel, decarboxylative Michael reaction between α-substituted azlactones and chromone-3-carboxylic acids is described. The reaction proceeds in a sequence Michael addition followed by decarboxylative deprotonation, and it results in the formation of chromanones bearing an azlactone structural unit. The possibility of transforming an azlactone moiety into a protected α,α-disubstituted α-amino acid derivative is also demonstrated. MDPI 2019-07-15 /pmc/articles/PMC6681191/ /pubmed/31311096 http://dx.doi.org/10.3390/molecules24142565 Text en © 2019 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 Communication
Bojanowski, Jan
Sieroń, Lesław
Albrecht, Anna
Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction
title Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction
title_full Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction
title_fullStr Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction
title_full_unstemmed Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction
title_short Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction
title_sort enantioselective synthesis of chromanones bearing an α,α-disubstituted α-amino acid moiety via decarboxylative michael reaction
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6681191/
https://www.ncbi.nlm.nih.gov/pubmed/31311096
http://dx.doi.org/10.3390/molecules24142565
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