Fluorinative Difunctionalization of a Cyclooctene-Fused β-Lactam and Cyclooctene-Fused β-Amino Esters
Abstract The synthesis of novel arylfluorinated cyclic β-amino acid and β-lactam derivatives is accomplished. Studies on the Pd-catalyzed arylfluorination of the double bond of a cyclooctene-fused azetidine-2-one and various β-amino esters are performed under versatile experimental conditions. The arylfluorinative difunctionalization of a cyclooctene-fused β-lactam, performed with phenylboronic acid in the presence of Selectfluor, palladium diacetate, azacyclic ligands and different solvents, gave a separable mixture of fluorinated and non-fluorinated products. In contrast, arylfluorination of cyclooctane-β-amino esters, performed under similar conditions, proceed with full regio- and stereoselective control, leading to single phenyl-fluorinated products. Possible synthetic pathways for these transformations are also proposed.
Authors
- Lóránd Kiss (ORCID: https://orcid.org/0000-0003-2346-9816)
- Tamás T. Novák (ORCID: https://orcid.org/0000-0003-2687-2264)
- Pál Tamás Szabó (ORCID: https://orcid.org/0000-0003-2260-4641)
- Melinda Nonn
- Gábor Turczel (ORCID: https://orcid.org/0000-0002-6753-6796)
- Gábor Hornyánszky (ORCID: https://orcid.org/0000-0001-7895-9711)
- Santos Fustero (ORCID: https://orcid.org/0000-0002-7575-9439)
Institutions
- Centre for Drug Research and Development (CA)
- Universitat de València (ES)
- Budapest University of Technology and Economics (HU)
- Institute of Materials and Environmental Chemistry (HU)
- Institute of Organic Chemistry (HU)
- Hungarian Academy of Sciences (HU)
- HUN-REN Research Centre for Natural Sciences (HU)
Publication Details
- Journal
- Synthesis
- Published
- 2025-05-14
- DOI
- https://doi.org/10.1055/a-2609-9601
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- European Commission
- Magyar Tudományos Akadémia
- Nemzeti Kutatási Fejlesztési és Innovációs Hivatal