Attempts on Fluorinative Transformation of Some Functionalized Cycloalkene Scaffolds through Aziridination/Aziridine Opening Protocol

Novák, Tibor Tamás and Gömöry, Ágnes and Nonn, Melinda and Han, Jianlin and Kiss, Loránd (2024) Attempts on Fluorinative Transformation of Some Functionalized Cycloalkene Scaffolds through Aziridination/Aziridine Opening Protocol. SYNLETT, 35. ISSN 0936-5214

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Abstract

Studies on the transformations of some functionalized cycloalkene derivatives through their ring olefin bond aziridination/aziridine opening with fluoride are presented. The selected model compounds submitted to fluorinative functionalization were an amino ester and diesters with a cyclohexene skeleton as well as a cyclopentene-fused β-lactam. Functionalization proceeded across a substrate-directed diastereoselective olefin bond aziridination, followed by fluoride-mediated aziridine opening or intramolecular lactonization giving some fluorinated, amino ester or amino lactone derivatives.

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