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Issue 91, 2016
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Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions

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Abstract

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.

Graphical abstract: Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions

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Publication details

The article was received on 28 Sep 2016, accepted on 19 Oct 2016 and first published on 19 Oct 2016


Article type: Communication
DOI: 10.1039/C6CC07855A
Citation: Chem. Commun., 2016,52, 13353-13356
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    Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions

    O. E. Okoromoba, Z. Li, N. Robertson, M. S. Mashuta, U. R. Couto, C. F. Tormena, B. Xu and G. B. Hammond, Chem. Commun., 2016, 52, 13353
    DOI: 10.1039/C6CC07855A

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