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

Author:
Okoromoba, Otome E., Li, Zhou, Robertson, Nicole, Mashuta, Mark S., Couto, Uenifer R., Tormena, Cláudio F., Xu, Bo, Hammond, Gerald B.
Source:
Chemical communications 2016 v.52 no.91 pp. 13353-13356
ISSN:
1364-548X
Subject:
chemical reactions, ethyleneimine, moieties, regioselectivity, stereochemistry
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.
Agid:
6390100