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

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.