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Issue 1, 2017
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Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis

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Abstract

A reagent-controlled enantioselectivity switch was uncovered in the asymmetric α-fluorination of β-ketocarbonyls by a chiral primary amine catalyst. By a simple swap of fluorination reagents, both enantiomers of the quaternary fluorination adducts could be obtained with good yields and high enantioselectivity. Mechanistic studies disclosed dual H-bonding and electrostatic stereocontrolling modes for the catalysis.

Graphical abstract: Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis

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Publication details

The article was received on 14 Jul 2016, accepted on 25 Aug 2016 and first published on 26 Aug 2016


Article type: Edge Article
DOI: 10.1039/C6SC03109A
Citation: Chem. Sci., 2017,8, 621-626
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    Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis

    Y. You, L. Zhang and S. Luo, Chem. Sci., 2017, 8, 621
    DOI: 10.1039/C6SC03109A

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