Direct asymmetric hydrogenation of 2-oxo-4-arylbut-3-enoic acids.

doi:10.1021/jo101084t

Paper

Direct asymmetric hydrogenation of 2-oxo-4-arylbut-3-enoic acids.

Published Aug 11, 2010 · Lvfeng Zhu, Qinghua Meng, W. Fan

The Journal of organic chemistry

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24

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0

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Abstract

A challenging direct asymmetric hydrogenation of (E)-2-oxo-4-arylbut-3-enoic acids to give 2-hydroxy-4-arylbutanoic acids (85.4-91.8% ee) was achieved with a Ru catalyst based on SunPhos as the chiral ligand. Further investigation of the reaction revealed that partial isomerization of 2-hydroxy-4-arylbutenoic acids was involved in the hydrogenation process. Employing the reaction conditions to the hydrogenation of 2-oxo-4-phenylbutanoic acid resulted in better enantioselectivity (91.8% ee) and efficiency (TON = 2000, TOF = 200 h(-1)), which offers a useful method for the synthesis of a common intermediate for ACE inhibitors.

Study Snapshot

Direct asymmetric hydrogenation of 2-oxo-4-arylbut-3-enoic acids with a Ru catalyst based on SunPhos enables efficient synthesis of 2-hydroxy-4-arylbutanoic acids, a common intermediate for ACE inhibitors.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Direct asymmetric hydrogenation of 2-oxo-4-arylbut-3-enoic acids.

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