Synthesis of Calix[4]proline Derivatives and Their Chiral Recognition for Enantiomers of Mandelic Acid

doi:10.6023/cjoc201502018

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (7): 1531-1536.DOI: 10.6023/cjoc201502018 Previous Articles Next Articles

Notes

杯[4]脯氨酸衍生物的合成及其对扁桃酸对映异构体的手性识别

李正义^a, 周坤^a, 来源^a, 孙小强^a, 王乐勇^b

a 常州大学石油化工学院江苏省绿色催化材料与技术重点实验室常州 213164;
b 超分子化学与智能材料实验室南京大学化学化工学院南京 210093

收稿日期:2015-02-10 修回日期:2015-03-02 发布日期:2015-03-19
通讯作者: 孙小强, 王乐勇 E-mail:sunxiaoqiang@yahoo.com,Lywang@nju.edu.cn
基金资助:
国家自然科学基金(No. 21002009)、江苏省高校自然科学研究重大项目(Nos. 12KJA150002, 14KJA150002)、江苏省优势学科和江苏省青蓝工程资助项目

Synthesis of Calix[4]proline Derivatives and Their Chiral Recognition for Enantiomers of Mandelic Acid

Li Zhengyi^a, Zhou Kun^a, Lai Yuan^a, Sun Xiaoqiang^a, Wang Leyong^b

a Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164;
b Laboratory for Supramolecular Chemistry and Dynamic Materials, School of Chemistry and Chemical Engineering, Nanjing Universty, Nanjing 210093

Received:2015-02-10 Revised:2015-03-02 Published:2015-03-19
Supported by:
Project supported by the NSFC (No. 21002009), Major Program for the Natural Science Research of Jiangsu Colleges and Universities (Nos. 12KJA150002, 14KJA150002), Priority Academic Program Development of Jiangsu Higher Education Institution (PAPD), and Qing Lan Project of Jiangsu Province.

1. Synthesis of Calix[4]proline Derivatives and Their Chiral Recognition for Enantiomers of Mandelic Acid.PDF(5159KB)

Abstract

Five chiral calix[4]proline derivatives were designed and synthesized from aminocalix[4]arenes, and their structures were characterized by ¹H NMR, ¹³C NMR, IR, ESI-MS and elemental analysis. The chiral recognition ability for enantiomers of mandelic acid was investigated by NMR techniques, and the results showed that 5,11-diprolinamides substituted calix[4]arene 2b could well and selectively recognize the two enantiomers of mandelic acid (K_L/K_D≈94). A possible recognition mechanism was proposed, which was constructed by cooperative multi-supramolecular interactions including intermolecular acid-base, hydrogen bond and π···π stacking interactions.

Key words: calix[4]arene, L-proline, mandelic acid, chiral recognition, NMR

Cite this article

Li Zhengyi, Zhou Kun, Lai Yuan, Sun Xiaoqiang, Wang Leyong. Synthesis of Calix[4]proline Derivatives and Their Chiral Recognition for Enantiomers of Mandelic Acid[J]. Chin. J. Org. Chem., 2015, 35(7): 1531-1536.

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杯[4]脯氨酸衍生物的合成及其对扁桃酸对映异构体的手性识别

Synthesis of Calix[4]proline Derivatives and Their Chiral Recognition for Enantiomers of Mandelic Acid

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