Efficient synthesis and resolution of a series of meta-substituted inherently chiral aminocalix[4]arene derivatives have been described. Consequently,the meta-nitro,bromo and chloro substituted inherently chiral calix[4]arenes could be directly synthesized by the nitration,bromination,and chlorination of the acylating product of aminocalix[4]arene. meta-Cyano and phenyl substituted inherently chiral aminocalix[4]arenes were readily obtained by the nucleophilic substitution reaction or Suzuki coupling reaction from the meta-bromo substituted one under the Pd-catalyzed conditions. For kinetic resolution of the racemic inherently chiral aminocalix[4]arenes,it was found that the electron-withdrawing ability of substituent was helpful to improving the resolution efficiency of the acylation process,and the kinetic resolution could be efficiently applied to the resolution of meta-nitro substituted inherently chiral aminocalix[4]arene,providing (cS)-or (cR)-isomer in up to 95% or 99.9% ee value,respectively,with the corresponding chiral acylating reagent. Moreover,by introduction of the chiral auxiliary,enantiopure antipodes of meta-cyano and phenyl substituted inherently chiral aminocalix[4]arenes could also be readily obtained. These enantiopure amino-calix[4]arenes are potential building blocks for constructing novel chiral receptors and asymmetric catalysts. Efficient synthesis and resolution of a series of meta-substituted inherently chiral aminocalix [4] arene derivatives have been described. Effects, the meta-nitro, bromo and chloro substituted inherently chiral calix [4] arenes could be directly synthesized by the nitration, bromination , and chlorination of the acylating product of aminocalix [4] arene. Meta-Cyano and phenyl substituted inherently chiral aminocalix [4] arenes were readily obtained by the nucleophilic substitution reaction or Suzuki coupling reaction from the meta-bromo substituted one under the Pd- catalyzed conditions. For kinetic resolution of the racemic inherently chiral aminocalix [4] arenes, it was found that the electron-withdrawing ability of any was helpful to improving the resolution efficiency of the acylation process, and the kinetic resolution could be able applied to the resolution of meta-nitro substituted inherently chiral aminocalix [4] arene, providing (cS) -or (cR) -isomer in up to 95% or 99.9% ee valu These enantiopure amino-calix [4] arenes could also be readily obtained. These enantiopure amino-calix [4] arenes are potential building blocks for constructing novel chiral receptors and asymmetric catalysts.