Highly enantioselective sequential hydrogenation of ethyl 2-oxo-4-arylbut-3-enoate to ethyl 2-hydroxy-4-arylbutyrate |
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Authors: | Meng Qinghua Zhu Lufeng Zhang Zhaoguo |
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Institution: | School of Chemistry and Chemical Technology, Shanghai Jiaotong University, 800 Dongchuan Road, Shanghai 200240, China. |
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Abstract: | The hydrogenation of (E)-ethyl 2-oxo-4-arylbut-3-enoate with NH2Me2](+){RuCl (S)-SunPhos]}2(mu-Cl3)] gave ethyl 2-hydroxy-4-arylbutyrate with 94-96% ee. Further investigation has proved that the hydrogenation proceeded via a sequential hydrogenation of CO and CC bonds, which is sensitive to the reaction temperature. Hydrolysis of ethyl 2-hydroxy-4-phenylbutyrate (ee 93%) provided the 2-hydroxy-4-phenylbutyric acid with 81% yield at 99% ee after a single recrystallization from 1,2-dichloroethylene. |
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