/ E-Alerts

Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex

Maurizio Iannuzzi, Thomas Hohmann, Michael Dyrks, Kilian Haoues, Katarzyna Salamon-Krokosz and Beate Koksch

Beilstein J. Org. Chem. 2025, 21, 659–669. https://doi.org/10.3762/bjoc.21.52

Supporting Information

Supporting Information File 1: NMR spectra and HPLC chromatograms.
Format: PDF	Size: 1.0 MB	Download

Cite the Following Article

Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex

Maurizio Iannuzzi, Thomas Hohmann, Michael Dyrks, Kilian Haoues, Katarzyna Salamon-Krokosz and Beate Koksch

Beilstein J. Org. Chem. 2025, 21, 659–669. https://doi.org/10.3762/bjoc.21.52

How to Cite

Iannuzzi, M.; Hohmann, T.; Dyrks, M.; Haoues, K.; Salamon-Krokosz, K.; Koksch, B. Beilstein J. Org. Chem. 2025, 21, 659–669. doi:10.3762/bjoc.21.52

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

File format:

RIS

BibTeX

Include:

Citation for the article above

Citation and complete reference list for the article above

Download

TY  - JOUR
A1  - Iannuzzi, Maurizio
A1  - Hohmann, Thomas
A1  - Dyrks, Michael
A1  - Haoues, Kilian
A1  - Salamon-Krokosz, Katarzyna
A1  - Koksch, Beate
T1  - Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex
JF  - Beilstein Journal of Organic Chemistry
PY  - 2025///
VL  - 21
SP  - 659
EP  - 669
SN  - 1860-5397
DO  - 10.3762/bjoc.21.52
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.21.52
KW  - chiral nickel complexes
KW  - fluorinated amino acids
KW  - gram-scale amino acid synthesis
KW  - stereoselective synthesis
N2  - Fluorinated amino acids are essential building blocks in the spheres of protein engineering and medicinal chemistry. In the last decades, a large number of different synthetic strategies have been developed to produce a large variety of fluorinated amino acids. Still, obtaining fluorinated amino acids in great quantities can be challenging, or the corresponding pathways are heavily time-consuming and synthetically challenging. In this context, chiral Ni(II) complexes can be powerful tools to obtain tailor‑made non‑canonical amino acids. In this work, we wanted to take advantage of this strategy and extend the range of this method to include additional fluorinated amino acids. We synthesized two fluorinated analogs of phenylalanine, which are still unexplored in the context of peptide and protein chemistry. Furthermore, both diastereomers of trifluoroleucine were synthesized, demonstrating that the described strategy can also be applied to synthesize enantio‑ and diastereomerically pure γ‑branched fluorinated amino acids. This work further underlines the importance of chiral Ni(II) complexes in the synthesis of fluorinated amino acids.
ER  -

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG	Size: 12.9 MB	Download

Back To Article

Other Beilstein-Institut Open Science Activities

aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)