Direct Asymmetric Hydrogenation of 2-Oxo-4-arylbut-3-enoic Acids

作者：Zhu, Lvfeng; Meng, Qinghua; Fan, Weizheng; Xie, Xiaomin; Zhang, Zhaoguo^*

来源：Journal of Organic Chemistry, 2010, 75(17): 6027-6030.

DOI：10.1021/jo101084t

• ACE inhibitors
• Asymmetric hydrogenation
• Chiral ligand
• Hydrogenation process
• Reaction conditions
• Ru catalysts

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.

• 出版日期2010-9-3
• 单位南京理工大学; 上海交通大学