Fluorinative Difunctionalization of a Cyclooctene-fused beta-Lactam and Cyclooctene-fused beta-Amino Esters

Novák, Tamás T. and Turczel, Gábor and Hornyánszky, Gábor and Szabó, Pál Tamás and Kiss, Loránd and Fustero, Santos and Nonn, Melinda (2025) Fluorinative Difunctionalization of a Cyclooctene-fused beta-Lactam and Cyclooctene-fused beta-Amino Esters. SYNTHESIS: JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY, 57. pp. 2391-2398. ISSN 0039-7881

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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.

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