Kinetic resolution of 2,2-difluoro-3-hydroxy-3-aryl-propionates catalyzed by organocatalyst (R)-benzotetramisole |
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| Authors: | Hui Zhou Peiran Chen |
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| Affiliation: | a Laboratory of Organic Fluorine Chemistry, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 Renmin Road North, Songjiang District, Shanghai 201620, China
b State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China |
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| Abstract: | Kinetic resolution of a series of ethyl 2,2-difluoro-3-hydroxy-3-aryl-propionates catalyzed by (R)-benzotetramisole has been performed. It was found that when the aryl group was phenyl or phenyl substituted with electron-donating group (such as -Me, -OMe, and -SMe) or naphthyl groups, the enantio-selectivity factor (s) could reach 20 or higher; electron-withdrawing (such as fluorine) substitution on the benzene ring dramatically lowers the s value. Kinetic resolution in preparative scale for some of the substrates demonstrated the applicability of this method. |
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