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L-脯氨酸修饰的Ru-PPh₃/γ-Al₂O₃催化芳香酮不对称加氢反应

Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by L-Proline-Modified Ru-PPh₃/γ-Al₂O₃ Catalyst

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【Author】 XIONG Wei1,LIU Derong1,JIA Yun1,QIN Ruixiang1,QIU Huidong1,WANG Jinbo1,LI Xianjun2 1College of Chemistry and Chemical Engineering,Chongqing University of Science and Technology,Chongqing 401331,China 2Key Laboratory of Green Chemistry and Technology of Ministry of Education,Institute of Homogeneous Catalysis,College of Chemistry,Sichuan University,Chengdu 610064,Sichuan,China

【机构】重庆科技学院化学化工学院；四川大学化学学院有机金属络合催化研究所绿色化学及技术教育部重点实验室；

【摘要】以L-脯氨酸为修饰剂,研究了膦配体稳定的Ru-PPh3/γ-Al2O3催化剂催化芳香酮不对称加氢反应,考察了不同稳定剂、L-脯氨酸浓度、KOH浓度、反应温度和氢气压力等因素对加氢反应的影响.结果表明,天然手性化合物L-脯氨酸对Ru-PPh3/γ-Al2O3催化剂具有较好的修饰作用,在优化反应条件下,苯乙酮加氢产物(S)-α-苯乙醇对映选择性达59.5%.L-脯氨酸不仅具有手性诱导作用,而且与KOH之间存在协同作用.催化剂循环使用5次,产物对映选择性没有明显下降.更多还原

【Abstract】 The asymmetric hydrogenation of aromatic ketones catalyzed by L-proline-modified Ru-PPh3/γ-Al2O3 was investigated. The ef-fects of reaction conditions on the asymmetric hydrogenation of acetophenone were discussed in detail. The results indicated that natural chiral compound L-proline has a good modification effect on the Ru-PPh3/γ-Al2O3 catalyst. Under the optimum conditions,the conversion of acetophenone was up to 100%,and the enantioselectivity for the formation of(R) -phenyl ethanol was 59.5%. The synergistic effect between L-proline and KOH was observed. The chiral alcohol products could be easily separated by centrifugation. The catalyst was reused several times without remarkable change of enantioselectivity.更多还原