Projects per year
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 |
---|---|
Article number | 131896 |
Journal | Tetrahedron |
Volume | 81 |
Early online date | 23 Dec 2020 |
DOIs | |
Publication status | Published - 12 Feb 2021 |
Bibliographical note
Funding Information:The authors would like to acknowledge Anna Kinsella for obtaining preliminary results. This work was supported by the Engineering and Physical Sciences Research Council EP/R020752/1 . A.J.C. thanks the Royal Society for a University Research Fellowship ( UF150533 ) and the University of Bath for generous financial support.
Publisher Copyright:
© 2020 Elsevier Ltd
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
Funding
The authors would like to acknowledge Anna Kinsella for obtaining preliminary results. This work was supported by the Engineering and Physical Sciences Research Council EP/R020752/1 . A.J.C. thanks the Royal Society for a University Research Fellowship ( UF150533 ) and the University of Bath for generous financial support.
Keywords
- Bioisosteres
- C–H functionalisation
- Photoredox catalysis
- γ-Aminophosphonates
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
Fingerprint
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
- 3 Finished
-
A Radical Approach to C-H Alkylation
Cresswell, A. (PI)
Engineering and Physical Sciences Research Council
20/01/20 → 31/03/23
Project: Research council
-
Nucleophilic alkaline earth boryls: from conception and theory to application
Hill, M. (PI), Cresswell, A. (CoI) & McMullin, C. (Researcher)
Engineering and Physical Sciences Research Council
1/05/18 → 31/07/22
Project: Research council
-
UR Fellowship for Alex Cresswell - Better than Boron? Silicon-Mediated Aromatic Functionalisation
Cresswell, A. (PI)
1/10/16 → 31/03/22
Project: Research council
Equipment
-
Avance III 400 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (9West)
Material and Chemical Characterisation (MC2)Facility/equipment: Equipment