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The Last Decade of Optically Active α-Aminophosphonates

α-Aminophosphonates and related compounds are important due to their real and potential biological activity. α-Aminophosphonates may be prepared by the Kabachnik–Fields condensation of oxo compounds, amines and dialkyl phosphites, or by the aza-Pudovik addition of the same P-reagents to imines. In t...

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Detalles Bibliográficos
Autores principales: Varga, Petra R., Keglevich, György
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10459122/
https://www.ncbi.nlm.nih.gov/pubmed/37630402
http://dx.doi.org/10.3390/molecules28166150
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author Varga, Petra R.
Keglevich, György
author_facet Varga, Petra R.
Keglevich, György
author_sort Varga, Petra R.
collection PubMed
description α-Aminophosphonates and related compounds are important due to their real and potential biological activity. α-Aminophosphonates may be prepared by the Kabachnik–Fields condensation of oxo compounds, amines and dialkyl phosphites, or by the aza-Pudovik addition of the same P-reagents to imines. In this review, the methods that allow for the synthesis of α-aminophosphonates with optical activity are surveyed. On the one hand, optically active catalysts or ligands may induce enantioselectivity during the Kabachnik–Fields reaction. On the other hand, asymmetric catalysis during the aza-Pudovik reaction, or hydrogenations of iminophosphonates, may prove to be a useful tool. Lastly yet importantly, it is possible to start from optically active reagents that may be associated with diastereoselectivity. The “green” aspects of the different syntheses are also considered.
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spelling pubmed-104591222023-08-27 The Last Decade of Optically Active α-Aminophosphonates Varga, Petra R. Keglevich, György Molecules Review α-Aminophosphonates and related compounds are important due to their real and potential biological activity. α-Aminophosphonates may be prepared by the Kabachnik–Fields condensation of oxo compounds, amines and dialkyl phosphites, or by the aza-Pudovik addition of the same P-reagents to imines. In this review, the methods that allow for the synthesis of α-aminophosphonates with optical activity are surveyed. On the one hand, optically active catalysts or ligands may induce enantioselectivity during the Kabachnik–Fields reaction. On the other hand, asymmetric catalysis during the aza-Pudovik reaction, or hydrogenations of iminophosphonates, may prove to be a useful tool. Lastly yet importantly, it is possible to start from optically active reagents that may be associated with diastereoselectivity. The “green” aspects of the different syntheses are also considered. MDPI 2023-08-20 /pmc/articles/PMC10459122/ /pubmed/37630402 http://dx.doi.org/10.3390/molecules28166150 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Varga, Petra R.
Keglevich, György
The Last Decade of Optically Active α-Aminophosphonates
title The Last Decade of Optically Active α-Aminophosphonates
title_full The Last Decade of Optically Active α-Aminophosphonates
title_fullStr The Last Decade of Optically Active α-Aminophosphonates
title_full_unstemmed The Last Decade of Optically Active α-Aminophosphonates
title_short The Last Decade of Optically Active α-Aminophosphonates
title_sort last decade of optically active α-aminophosphonates
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10459122/
https://www.ncbi.nlm.nih.gov/pubmed/37630402
http://dx.doi.org/10.3390/molecules28166150
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