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Synthesis
DOI: 10.1055/a-2609-9601
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Fluorinative Difunctionalization of Selected Cyclooctene-Fused Beta-Lactams and Beta-Amino Esters

Tamás T. Novák
1   Institute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences, Budapest, Hungary (Ringgold ID: RIN280964)
2   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary (Ringgold ID: RIN61810)
,
Lorand Kiss
3   Institute of Organic Chemistry, Research Centre for Natural Sciences, Budapest, Hungary (Ringgold ID: RIN280964)
,
Gábor Turczel
4   Centre for Structural Sciences, HUN-REN Research Centre for Natural Sciences, Budapest, Hungary (Ringgold ID: RIN280964)
,
Gábor Hornyánszky
5   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics Faculty of Chemical Technology and Biotechnology, Budapest, Hungary (Ringgold ID: RIN415618)
,
Pál T Szabó
6   MS Metabolomics Research Group, Centre for Structural Science, Research Centre for Natural Sciences, Budapest, Hungary (Ringgold ID: RIN280964)
,
Santos Fustero
7   Organic Chemistry, University of Valencia, Burjassot, Spain
,
MELINDA NONN
8   INSTITUTE OF MATERIALS AND ENVIRONMENTAL CHEMISTRY, Research Centre for Natural Sciences Institute of Materials and Environmental Chemistry, Budapest, Hungary (Ringgold ID: RIN557117)
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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.



Publication History

Received: 11 April 2025

Accepted after revision: 14 May 2025

Accepted Manuscript online:
14 May 2025

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