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Issue 23, 2013
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Asymmetric hydrogenation of β-amino ketones with the bimetallic complex RuPHOX-Ru as the chiral catalyst

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Abstract

Asymmetric hydrogenations of a series of β-amino ketones were carried out with a bimetallic complex (RuPHOX-Ru) as the chiral catalyst. Almost all the reactions (performed in a mixed solvent system of toluene and H2O in the presence of KOH) gave quantitative conversions into their respective products with up to 99.9% ee. The RuPHOX-Ru catalyst is stable to both moisture and air. The procedure has the benefits of being inexpensive, environmentally friendly and highly efficient. Under a relatively low catalyst loading (TON = 2000), key intermediates of fluoxetine, tomoxetine and nisoxetine could be obtained in quantitative yield and in up to 99.9% ee. This methodology represents a promising alternative to the synthesis of the aforementioned drugs and their analogues.

Graphical abstract: Asymmetric hydrogenation of β-amino ketones with the bimetallic complex RuPHOX-Ru as the chiral catalyst

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Publication details

The article was received on 22 Jan 2013, accepted on 11 Apr 2013 and first published on 16 Apr 2013


Article type: Paper
DOI: 10.1039/C3OB40135A
Citation: Org. Biomol. Chem., 2013,11, 3855-3861
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    Asymmetric hydrogenation of β-amino ketones with the bimetallic complex RuPHOX-Ru as the chiral catalyst

    J. Wang, D. Liu, Y. Liu and W. Zhang, Org. Biomol. Chem., 2013, 11, 3855
    DOI: 10.1039/C3OB40135A

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