Efficient access to chiral 1,2-amino alcohols via Ir/f-amphox-catalyzed asymmetric hydrogenation of α-amino ketones
Literature Information
Publication Date
2017-04-24
DOI
10.1039/C7QO00237H
Impact Factor
5.281
Authors
Yang Hu, Weilong Wu, Xiu-Qin Dong
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
1,3(2H,4H)-Isoquinolinedione, 7-amino-4,4-dimethyl-
CAS Number:
14576-22-8
Molecular Formula:
C11H12N2O2
![(3R,5R)-1-[(Benzyloxy)carbonyl]-5-methyl-3-piperidinecarboxylic acid structure](https://static.chemtradehub.com/structs/126/1269757-29-0-c552.webp "(3R,5R)-1-[(Benzyloxy)carbonyl]-5-methyl-3-piperidinecarboxylic acid structure")
(3R,5R)-1-[(Benzyloxy)carbonyl]-5-methyl-3-piperidinecarboxylic acid
CAS Number:
1269757-29-0
Molecular Formula:
C15H19NO4
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