Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions. Issue 91 (26th October 2016)

• Record Type: Journal Article
• Authors: Okoromoba, Otome E.; Li, Zhou; Robertson, Nicole; Mashuta, Mark S.; Couto, Uenifer R.; Tormena, Cláudio F.; Xu, Bo; Hammond, Gerald B.
• Is Part Of: Chemical communications. Volume 52:Issue 91(2016)
• Page Start: 13353
• Page End: 13356
• Publication Date: 2016-10-26
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c6cc07855a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : DMPU–HF demonstrates good reactivity and regioselectivity in conversion of aziridines into biologically important β-fluoroamines. The stereochemistry of aziridine-opening was found to be depend greatly on substitution pattern. 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.