Efficient access to chiral 1, 2-amino alcohols via Ir/f-amphox-catalyzed asymmetric hydrogenation of α-amino ketones. Issue 8 (4th May 2017)

• Record Type: Journal Article
• Authors: Hu, Yang; Wu, Weilong; Dong, Xiu-Qin; Zhang, Xumu
• Is Part Of: Organic chemistry frontiers. Volume 4:Issue 8(2017)
• Page Start: 1499
• Page End: 1502
• Publication Date: 2017-05-04
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c7qo00237h
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : We successfully developed the iridium/f-amphox-catalyzed asymmetric hydrogenation of α-amino ketones to prepare chiral 1, 2-amino alcohols with excellent results. 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.