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.
ZhengYi Li MingYu Teng JieJie Ma Ji Huang LeYong WangYi Pan
