Novák, Tibor Tamás and Turczel, Gábor and Hornyánszky, Gábor and Szabó, Pál T. and Kiss, Loránd and Fustero, Santos and Nonn, Melinda (2025) Fluorinative Difunctionalization of a Cyclooctene-Fused β-Lactam and Cyclooctene-Fused β-Amino Esters. SYNTHESIS-STUTTGART, 57 (15). pp. 2391-2398. ISSN 0039-7881
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Abstract
Synthesis of novel arylfluorinated cyclic β-amino acid derivatives and β-lactams has been accomplished. Thestudies on the Pd-catalyzed arylfluorination of the ring olefin bond of cyclooctene-fused azetidine-2-one and beta-amino esters with cyclooctene skeleton were performed under versatile experimental conditions. The arylfluorinative difunctionalization of cyclooctene-fused β-lactam, performed with phenylboronic acid, in the presence of Selectfluor, azacyclic ligands, and solvents, gave a separable mixture of various fluorinated and non-fluorinated products. In contrast, arylfluorination of cyclooctane-β-amino esters proceeded under similar conditions, with full regio- and stereoselective manners leading to a sole phenyl-fluorinated compound. Possible synthetic pathways regarding the outcome of these types of transformation are also proposed.
| Item Type: | Article |
|---|---|
| Additional Information: | Funding Agency and Grant Number: Nemzeti Kutatasi Fejlesztesi es Innovacios Hivatal (NKFIH/OTKA); National Research, Development and Innovation Office) of Hungary [FK 145394, K 142266]; European Union [RRF-2.3.1-21-2022-00015]; Janos Bolyai Research Scholarship from Magyar Tudomanyos Akademia (Hungarian Academy of Sciences) Funding text: The authors gratefully acknowledge financial support from the Nemzeti Kutatasi Fejlesztesi es Innovacios Hivatal (NKFIH/OTKA) (National Research, Development and Innovation Office) of Hungary (FK 145394 and K 142266). We are also grateful for the support providedby the European Union (Project no. RRF-2.3.1-21-2022-00015). This work was supported by the Janos Bolyai Research Scholarship to M.N.from Magyar Tudomanyos Akademia (Hungarian Academy of Sciences). |
| Uncontrolled Keywords: | amino acids, arylation, difunctionalization, fluorine, lactams |
| Subjects: | Q Science / természettudomány > QD Chemistry / kémia |
| SWORD Depositor: | MTMT SWORD |
| Depositing User: | MTMT SWORD |
| Date Deposited: | 12 Sep 2025 11:16 |
| Last Modified: | 12 Sep 2025 11:16 |
| URI: | https://real.mtak.hu/id/eprint/224088 |
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