Highly enantioselective hydrogenation of 2-oxo-4-arybutanoic acids to 2-hydroxy-4-arylbutanoic acids

The Ru-catalyzed asymmetric hydrogenation of 2-oxo-4-arybutanoic acids to afford 2-hydroxy-4-arybutanoic acids was accomplished by employing SunPhos as chiral ligand and 1 M aq HBr as additive. The high enantioselectivities (88.4%–92.6% ee) and efficiency (TON=10,000, TOF=300 h −1) make this method...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2011-08, Vol.67 (34), p.6186-6190
Main Authors: Zhu, Lufeng, Chen, Houhe, Meng, Qinghua, Fan, Weizheng, Xie, Xiaomin, Zhang, Zhaoguo
Format: Article
Language:English
Subjects:
Additive
Additives
Aliphatic compounds
Asymmetric hydrogenation
Asymmetry
Chemistry
Exact sciences and technology
Hydrogenation
Inhibitors
Ligands
Organic chemistry
Preparations and properties
Ruthenium
SunPhos
Synthesis (chemistry)
Tetrahedrons
α-Keto acid
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The Ru-catalyzed asymmetric hydrogenation of 2-oxo-4-arybutanoic acids to afford 2-hydroxy-4-arybutanoic acids was accomplished by employing SunPhos as chiral ligand and 1 M aq HBr as additive. The high enantioselectivities (88.4%–92.6% ee) and efficiency (TON=10,000, TOF=300 h −1) make this method efficient for the synthesis of an important intermediate, ( R)-2-hydroxy-4-phenylbutanoic acid, for ACE inhibitors. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.06.071