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Issue 8, 2017
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Efficient access to chiral 1,2-amino alcohols via Ir/f-amphox-catalyzed asymmetric hydrogenation of α-amino ketones

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Abstract

Tridentate f-amphox ligands were successfully applied to the iridium-catalyzed asymmetric hydrogenation of various α-amino ketones to afford a series of chiral 1,2-amino alcohols with excellent results (all products up to >99% conversion and >99% ee, TON up to 500 000). The products chiral 1,2-amino alcohols are important motifs in many pharmaceuticals, chiral auxiliaries and ligands. Our catalytic system provided an efficient synthetic route to prepare an important chiral intermediate of (S)-phenylephrine with practical industrial potential (up to 200 000 TON and >99% ee), which is the enantiomer of a famous α-adrenergic receptor agonist.

Graphical abstract: Efficient access to chiral 1,2-amino alcohols via Ir/f-amphox-catalyzed asymmetric hydrogenation of α-amino ketones

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Publication details

The article was received on 25 Mar 2017, accepted on 22 Apr 2017 and first published on 24 Apr 2017


Article type: Research Article
DOI: 10.1039/C7QO00237H
Citation: Org. Chem. Front., 2017,4, 1499-1502
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    Efficient access to chiral 1,2-amino alcohols via Ir/f-amphox-catalyzed asymmetric hydrogenation of α-amino ketones

    Y. Hu, W. Wu, X. Dong and X. Zhang, Org. Chem. Front., 2017, 4, 1499
    DOI: 10.1039/C7QO00237H

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