Efficient and practical asymmetric synthesis of isopropyl (R)-3-(3′,4′-dihydroxyphenyl)-2-hydroxypropanoate and its enantiomer |
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| Authors: | Ming Chen Hui Chen Yuzhen WangHaibo Wang Yefei NanXiaohui Zheng Ru Jiang |
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| Institution: | a Department of Medicinal Chemistry and Pharmaceutical analysis, School of Pharmacy, Fourth Military Medical University, Xi’an 710032, China
b Key Laboratory of Resource Biology and Biotechnology in Western China and College of Life Sciences, Northwest University, Xi’an 710069, China |
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| Abstract: | The highly enantioselective synthesis of (R)-isopropyl 3-(3′,4′-dihydroxyphenyl)-2-hydroxypropanoate and its enantiomer has been achieved starting from 3,4-dihydroxybenzaldehyde. The stereogenic centers were established through asymmetric dihydroxylation of (E)-isopropyl 3,4-bis(benzyloxy) cinnamate. A convenient manipulation in selective catalytic hydrogenation and deprotection was also accomplished in HCl-iPrOH employing 10% Pd/C catalyst. |
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