Unprecedented synthesis of chiral calix[4](aza)crowns and its potent encapsulating methanol  

作　　者：ZhengYi Li  MingYu Teng  JieJie Ma  Ji Huang  LeYong Wang Yi Pan 

机构地区：[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

出　　处：《Science China Chemistry》2009年第4期497-504,共8页中国科学（化学英文版）

基　　金：Supported by the National Basic Research Program of China (Grant No. 2007CB925103);the National Natural Science Foundation of China (Grant No. 20602017);NCET-07-0425

摘　　要：Unprecedented synthesis of chiral (aza)crown ethers of calix[4]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 ZnCl<SUB>2</SUB> Lewis acid at elevated temperature in a very efficient one-pot process. The cavity of calix[4](aza)crowns can encapsulate methanol molecules by O-H&#8943;&#1087; interaction, which has been confirmed by X-ray crystal structures and ESI-MS.Unprecedented synthesis of chiral (aza)crown ethers of calix[4]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 calix[4](aza)crowns can encapsulate methanol molecules by O-H...π interaction,which has been confirmed by X-ray crystal structures and ESI-MS.

关 键 词：CHIRAL (aza)crown dinitrile 1 2-aminoalcohol X-ray crystal structure inclusion complex 

分 类 号：O621.3[理学—有机化学]