Design and Synthesis of Novel Chiral Imidazolium Cyclophanes and Their Enantioselective Recognition for α-Amino Acids and Their Derivatives

Chem. J. Chinese Universities

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Design and Synthesis of Novel Chiral Imidazolium Cyclophanes and Their Enantioselective Recognition for α-Amino Acids and Their Derivatives

GUO Sheng-Jin^1,2, LUO Kui¹, WANG Wen-Hai¹, ZHANG Shi-Yong¹, JIANG He-Yan¹,
LAN Jing-Bo¹, XIE Ru-Gang¹*

1. Department of Chemistry, Sichuan University, Chengdu 610064, China;
2. Department of Bioscience and Technology, Jinzhong College, Yuci 030600, China

Received:2005-08-18 Revised:1900-01-01 Online:2006-09-10 Published:2006-09-10
Contact: XIE Ru-Gang

Abstract

Abstract: A series of novel chiral imidazolium cyclophanes were synthesized from natural amino acids. (S)-2-(1-Imidazolyl)alkanoates(2) were prepared by cyclization and esterification. In the presence of DMAP and Et₃N. Alkanoates(2) reacted with ethylenediamine to yield compounds 3 with satisfactory yields. Compounds 3 reacted with 2,6-bis(bromomethyl)-4-chlorphenol, 1,3-bis(bromomethyl)benzene or 2,6-bis(bromomethyl)pyridine to afford dibromide salts under high dilution and anhydrous condition. Finally, the hexafluorophosphates (4—6) were obtained by treating the corresponding dibromide salts with a saturated aqueous solution of NH₄PF₆. The structures of the target compounds were confirmed by IR, ¹H NMR, MS, HRMS, and elemental analysis. These compounds featured large cavities and multipoint binding sites. UV spectroscopic titration experiments showed these chiral imidazolium cyclophanes exhibited good enantioselective recognition toward L- and D-amino acids and their derivatives.

Key words: Amino acid, Chiral imidazolium cyclophane, S ynthesis, Enantioselective recognition

CLC Number:

O626.23
O614

TrendMD:

GUO Sheng-Jin^1,2, LUO Kui¹, WANG Wen-Hai¹, ZHANG Shi-Yong¹, JIANG He-Yan¹,
LAN Jing-Bo¹, XIE Ru-Gang¹*. Design and Synthesis of Novel Chiral Imidazolium Cyclophanes and Their Enantioselective Recognition for α-Amino Acids and Their Derivatives[J]. Chem. J. Chinese Universities, doi: .

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Design and Synthesis of Novel Chiral Imidazolium Cyclophanes and Their Enantioselective Recognition for α-Amino Acids and Their Derivatives

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