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Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (11): 1695-1699. Previous Articles Next Articles
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程咏梅,徐刚,吴坚平,杨立荣*
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动态动力学拆分制备手性药物中间体的应用基础研究;高效脂肪酶调控机制及性能强化的基础研究;典型高效生物催化剂及其反应体系的开发;化学-酶法制备手性S-生物烯丙菊酯的关键技术研究
CHENG Yong-Mei, XU Gang, WU Jian-Ping, YANG Li-Rong
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A new and efficient dynamic kinetic resolution (DKR) process of 1-phenylethanol was developed with acid resin as racemization catalyst and lipase as resolution catalyst. Acid resin CD550 was shown to have excellent racemization activity and could racemize 100 mmol/L (S)-1-phenylethanol in 1.5 h at 60 ℃. When employing CD550 and complex acyl donors such as 1,2-diacetoxybenzene, 1,3-diacetoxybenzene and 3,5-dimethyl phenyl acetate instead of vinyl acetate as racemization catalyst and acyl donor respectively to the DKR of 1-phenylethanol, enantiomerically pure (R)-1-phenylethanol acetate could be obtained with excellent yield and ee values. During processing, the conversion and the selectivity of the DKR were successfully enhanced by using more complex acyl donors to inhibit the acid resin-catalyzed unslective transesterification. For instance, when 1,2-diacetoxybenzene as acyl donor, the conversion and the eep could reach above 99% and 90.5% after 10 h, respectively.
Key words: 1-phenylethanol, dynamic kinetic resolution, racemization, acyl donor
CHENG Yong-Mei, XU Gang, WU Jian-Ping, YANG Li-Rong. Dynamic Kinetic Resolution of 1-Phenylethanol Catalyzed by Lipase Coupled with Acid Resin[J]. Chin. J. Org. Chem., 2010, 30(11): 1695-1699.
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