Unprecedented synthesis of chiral calix[4](aza)crowns and its potent encapsulating methanol |
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| Authors: | ZhengYi Li MingYu Teng JieJie Ma Ji Huang LeYong Wang Yi Pan |
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| Institution: | (1) Key Laboratory of Mesoscopic Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China;(2) Xuzhou Medical College, Xuzhou, 221004, China |
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| Abstract: | Unprecedented synthesis of chiral (aza)crown ethers of calix4]arene derivatives bearing a carboxyl amide bridge was described.
The synthesis proceeds through condensation of the corresponding dinitriles with optically active 1,2-aminoalcohols, and is
catalyzed by the ZnCl2 Lewis acid at elevated temperature in a very efficient one-pot process. The cavity of calix4](aza)crowns can encapsulate
methanol molecules by O-H⋯п interaction, which has been confirmed by X-ray crystal structures and ESI-MS.
Supported by the National Basic Research Program of China (Grant No. 2007CB925103), the National Natural Science Foundation
of China (Grant No. 20602017), and NCET-07-0425 |
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| Keywords: | chiral calix[4](aza)crown dinitrile 1 2-aminoalcohol X-ray crystal structure inclusion complex |
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