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

Organic Chemistry Frontiers Pub Date: 2017-04-24 DOI: 10.1039/C7QO00237H

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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