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Issue 12, 2018
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Highly enantioselective Ir/f-amphox-catalyzed hydrogenation of ketoamides: efficient access to chiral hydroxy amides

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Abstract

Asymmetric synthesis of chiral hydroxy amides has been successfully accomplished by enantioselective catalytic hydrogenation of various prochiral α-, β-, γ-, δ-keto amides in the presence of an Ir/f-amphox catalyst with excellent results (up to >99% conversion and >99% ee). Furthermore, the asymmetric hydrogenation of 5-(4-fluorophenyl)-5-oxo-N-phenylpentanamide was found to proceed smoothly with only 0.002 mol% (S/C = 50 000) catalyst. The hydrogenation product was obtained with >99% conversion and >99% ee, and which is an important structural framework of the anti-hyperlipidemic drug Ezetimibe.

Graphical abstract: Highly enantioselective Ir/f-amphox-catalyzed hydrogenation of ketoamides: efficient access to chiral hydroxy amides

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Publication details

The article was received on 21 Mar 2018, accepted on 28 Apr 2018 and first published on 02 May 2018


Article type: Research Article
DOI: 10.1039/C8QO00307F
Citation: Org. Chem. Front., 2018,5, 2000-2003
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    Highly enantioselective Ir/f-amphox-catalyzed hydrogenation of ketoamides: efficient access to chiral hydroxy amides

    Y. Hu, X. Yin, Z. Chen, X. Dong and X. Zhang, Org. Chem. Front., 2018, 5, 2000
    DOI: 10.1039/C8QO00307F

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