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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2023
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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. |
format | Online Article Text |
id | pubmed-10459122 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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