Facile Conversion of α‐Amino Acids into α‐Amino Phosphonates by Decarboxylative Phosphorylation using Visible‐Light Photocatalysis
Abstract: Amino phosphonates exhibit potent inhibitory activity for a wide range of biological processes due to their specific structural and electronic properties, making them important in a plethora of applications, including as enzyme inhibitors, herbicides, antiviral, antibacterial, and antifungal agents. While the traditional synthesis of α‐amino phosphonates has relied on the multicomponent Kabachnik‐Fields reaction, we herein describe a novel and facile conversion of activated derivatives of α‐amino acids directly to their respective α‐amino phosphonate counterparts via a decarboxylative radical–polar crossover process enabled by the use of visible‐light organophotocatalysis. The novel method shows broad applicability across a range of natural and synthetic amino acids, operates under mild conditions, and has been demonstrated to successfully achieve the late‐stage functionalization of drug molecules.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Facile Conversion of α‐Amino Acids into α‐Amino Phosphonates by Decarboxylative Phosphorylation using Visible‐Light Photocatalysis ; day:04 ; month:08 ; year:2022 ; extent:1
Angewandte Chemie / International edition. International edition ; (04.08.2022) (gesamt 1)
- Creator
- DOI
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10.1002/anie.202207063
- URN
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urn:nbn:de:101:1-2022080515064576268864
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:21 AM CEST
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Associated
- Reich, Dominik
- Noble, Adam
- Aggarwal, Varinder K.
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Facile Conversion of α‐Amino Acids into α‐Amino Phosphonates by Decarboxylative Phosphorylation using Visible‐Light Photocatalysis
Visible-Light Photoredox-Catalyzed Giese Reaction: Decarboxylative Addition of Amino Acid Derived α-Amino Radicals to Electron-Deficient Olefins
Nickel‐Catalyzed Enantioselective Decarboxylative Acylation: Rapid, Modular Access to α‐Amino Ketones **
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