Issue 12, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
04 رجب 1439
Accepted
12 شعبان 1439
First published
16 شعبان 1439

Org. Chem. Front., 2018,5, 2000-2003

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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