Ru-Catalyzed asymmetric hydrogenation of alpha-ketoesters with CeCl3.7H2O as additive |
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Authors: | Sun Yanhui Wan Xiaobing Wang Jianping Meng Qinghua Zhang Hongwei Jiang Lijuan Zhang Zhaoguo |
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Institution: | State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, China. |
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Abstract: | reaction: see text] An efficient asymmetric hydrogenation of alpha-ketoesters is reported with use of a catalyst prepared from Ru((S)-3)(benzene)Cl]Cl and CeCl(3).7H(2)O. Alpha-hydroxy esters are obtained in up to 96% ee. The addition of CeCl(3).7H(2)O not only improves the enantioselectivity, but also enhances the stability of the catalyst. As a result, the hydrogenation of methyl benzoylformate affords the product with 92% ee with a substrate/catalyst ratio of 10 000. Hydrolysis of 2 provides the final compound with 83% yield at 99% ee after a single recrystallization from 1,2-dichloroethylene. |
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