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...

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Veröffentlicht in:Tetrahedron 2011-08, Vol.67 (34), p.6186-6190
Hauptverfasser: Zhu, Lufeng, Chen, Houhe, Meng, Qinghua, Fan, Weizheng, Xie, Xiaomin, Zhang, Zhaoguo
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container_end_page 6190
container_issue 34
container_start_page 6186
container_title Tetrahedron
container_volume 67
creator Zhu, Lufeng
Chen, Houhe
Meng, Qinghua
Fan, Weizheng
Xie, Xiaomin
Zhang, Zhaoguo
description 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]
doi_str_mv 10.1016/j.tet.2011.06.071
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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
title Highly enantioselective hydrogenation of 2-oxo-4-arybutanoic acids to 2-hydroxy-4-arylbutanoic acids
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