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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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Article information


Submitted
28 Sep 2016
Accepted
19 Oct 2016
First published
19 Oct 2016

Chem. Commun., 2016,52, 13353-13356
Article type
Communication

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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