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Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions.

Otome E OkoromobaZhou LiNicole RobertsonMark S MashutaUenifer R CoutoCláudio Francisco TormenaBo XuGerald B Hammond
Published in: Chemical communications (Cambridge, England) (2018)
We developed an efficient fluorination protocol that converts easily accessible aziridines into β-fluoroamines, which are important motifs in biologically active molecules. In contrast with traditional fluorination approaches, DMPU-HF has shown both higher reactivity and regioselectivity and good functional group tolerance; thus, a wide scope of β-fluoroamines can now be accessed conveniently. The stereochemical behavior of the ring opening depends on the substitution pattern of the aziridine substrate.
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