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

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.