Design of chiral calix arene for synthesis of optically-active unnatural amino acids by asymmetric complexation

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Optically-active large cyclic compounds were prepared from calix arenes. NMR analysis of a 1:1 complex between the chiral calix arene and a racemic tetraalkylamkmonium salt was examined. Each enantiomer of the tetraalkylammonium salt were observed separately in the spectrum. Asymmetric rearrangements of the tetraalkylammonium salts using the chiral calix arenes as an organo-catalyst were examined. The rearrangement products were successfully converted to the corresponding unnatural amino acids.