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
收稿日期: 2015-02-10
修回日期: 2015-03-02
网络出版日期: 2015-03-19
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
Received date: 2015-02-10
Revised date: 2015-03-02
Online 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.
李正义 , 周坤 , 来源 , 孙小强 , 王乐勇 . 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[J]. 有机化学, 2015 , 35(7) : 1531 -1536 . DOI: 10.6023/cjoc201502018
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 (KL/KD≈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
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