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Iron(II)-catalyzed intramolecular olefin aminofluorination
Journal article   Peer reviewed

Iron(II)-catalyzed intramolecular olefin aminofluorination

Deng-Fu Lu, Guan-Sai Liu, Cheng-Liang Zhu, Bo Yuan and Hao Xu
Organic letters, Vol.16(11), pp.2912-2915
06/06/2014
PMID: 24829034

Abstract

Amines - chemistry Alkenes - chemistry Stereoisomerism Iron - chemistry Halogenation Molecular Structure Catalysis Ligands
An iron(II)-catalyzed diastereoselective olefin aminofluorination is reported (dr up to >20:1). This new transformation applies a functionalized hydroxylamine and Et3N·3HF as the nitrogen and fluorine source, which facilitates the efficient synthesis of β-fluoro primary amines and amino acids from allylic alcohol derivatives. Preliminary mechanistic studies reveal that an iron-nitrenoid is a possible intermediate and that its reactivity and enantioselectivity can be efficiently modulated by ligands.

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