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

ABSTRACT: We developed an efficient fluorination protocol that converts easily accessible aziridines into ?-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 ?-fluoroamines can now be accessed conveniently. The stereochemical behavior of the ring opening depends on the substitution pattern of the aziridine substrate.

SUBMITTER: Okoromoba OE

PROVIDER: S-EPMC5104567 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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

Okoromoba Otome E OE Li Zhou Z Robertson Nicole N Mashuta Mark S MS Couto Uenifer R UR Tormena Cláudio F CF Xu Bo B Hammond Gerald B GB

Chemical communications (Cambridge, England) 20161101 91

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 su ...[more]

PMID: 27782265

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

Publications

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

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