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A new free recoverable and reusable mono-alkaloid-type ligand and its use in preparation of ethyl(2R,3S)-2,3-dihydroxy-3-phenylpropionate

A new free recoverable and reusable mono-alkaloid-type ligand and its use in preparation of ethyl(2R,3S)-2,3-dihydroxy-3-phenylpropionate
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摘要 A new free recoverable and reusable mono-alkaloid-type ligand has been synthesized by a simple method. With highly polar groups, the ligand can be recycled and reused eight times to prepare ethyl （2R,3S）-2,3-dihydroxy-3-phenylpropionate with high yield and ee via asymmetric dihydroxylation （AD） reaction. C 2009 Sheng Yong Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. A new free recoverable and reusable mono-alkaloid-type ligand has been synthesized by a simple method. With highly polar groups, the ligand can be recycled and reused eight times to prepare ethyl （2R,3S）-2,3-dihydroxy-3-phenylpropionate with high yield and ee via asymmetric dihydroxylation （AD） reaction. C 2009 Sheng Yong Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
作者 Qiao Feng Wang Hui Chen Yan Zhao Xiao Ye Li Sheng Yong Zhang
机构地区 Research Center of Chirotechnology
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2009年第7期763-766,共4页 中国化学快报（英文版）
基金 supported by the National Natural Science Foundation of China(No.20572131,20842007) Natural Science Basic Research Plan in Shaanxi Province of China(No.SJ08-ZT02) for financial support.
关键词 Cinchona alkaloid Recoverable and reusable ligand Ethyl （2R 3S）-2 3-dihydroxy-3-phenylpropionate Cinchona alkaloid Recoverable and reusable ligand Ethyl （2R,3S）-2,3-dihydroxy-3-phenylpropionate
分类号 TQ225.241 [化学工程—有机化工] V475 [航空宇航科学与技术—飞行器设计]
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参考文献9

  • 1M.V. Voronkov, A.V. Gontcharov, Z.M. Wang, Tetrahedron Lett. 44 (2003) 407.
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  • 9Mono-alkaloid-type ligand 1: mp 58-60 ℃ [α]D^25-3.25 (c 1, CHCl3); ^1H NMR (300 MHz, CDCl3, δ ppm): 1.01-1.91 (m, 6H), 2.08 (m, 6H), 2.52 (m, 2H), 2.73 (s, 2H), 3.05-3.83 (m, 6H), 6.09 (s, 1H), 6.71 (s, 2H), 7.08-7.10 (m, 4H), 7.79 (br, 2H), 8.34 (s, 1H). 13C NMR (75 MHz, CDCl3. δ ppm): 23.5, 26.9, 27.5, 37.4, 41.9, 53.7, 55.3, 59.7, 64.2, 64.8, 73.3, 73.8, 118.2, 121.3, 125.3, 125.9, 126.9, 127.2, 128.5 128.7, 130.8, 130.9, 132.6, 143.7, 144.2, 146.2, 157.5. HRMS (ESI): Calcd. For C27H32N206S (M+H^+): 513.2. found 513.1.
Chinese Chemical Letters
2009年 第7期

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