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Abstract
We report a simple photocatalytic protocol for the direct synthesis of γ-amino phosphonates via the α-C–H alkylation of unprotected, aliphatic primary amines with diethyl vinylphosphonate. These motifs are valuable bioisosteres of γ-amino acids and O-phosphorylated amino alcohols. Visible-light photoredox catalysis in combination with hydrogen atom transfer (HAT) catalysis is used to access the necessary α-amino radical intermediates for C–C bond formation. The procedure is also demonstrated on gram-scale in continuous flow for the synthesis of a racemic, protected derivative of the mGlu agonist 2-amino-4-phosphonobutyric acid (AP4).
Original language | English |
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Article number | 131896 |
Journal | Tetrahedron |
Volume | 81 |
Early online date | 23 Dec 2020 |
DOIs | |
Publication status | Published - 1 Feb 2021 |
Keywords
- Bioisosteres
- C–H functionalisation
- Photoredox catalysis
- γ-Aminophosphonates
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Dive into the research topics of 'γ-Amino phosphonates via the photocatalytic α-C–H alkylation of primary amines'. Together they form a unique fingerprint.Projects
- 2 Finished
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Nucleophilic alkaline earth boryls: from conception and theory to application
Hill, M., Cresswell, A. & McMullin, C.
Engineering and Physical Sciences Research Council
1/05/18 → 31/07/22
Project: Research council
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UR Fellowship for Alex Cresswell - Better than Boron? Silicon-Mediated Aromatic Functionalisation
1/10/16 → 31/03/22
Project: Research council