The Role of Amino Acid Esters and the Amide Group in the Chiral Induction Process by a Novel Monoamide‐Linked Monozinc Bisporphyrinate |
| |
| Authors: | Yinzhi Zhang Ben Ma Yong Wang Chuanjiang Hu |
| |
| Institution: | 1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China;2. State Key Lab & Coordination Chemistry Institute, Nanjing University, Nanjing 210093, P. R. China |
| |
| Abstract: | A monoamide‐linked monozinc bisporphyrinate for monodentate chiral guests was designed and synthesized. It was used as a host to complex with amino acid esters; the resulting CD spectra showed typical bisignate shape, which suggest the ability to transfer chirality from amino acid esters. The molecular structure of the host indicates that amino acid esters function as monodentate ligands in the host‐guest complex. 1H NMR spectroscopic studies suggest formation of a hydrogen bond between the amide NH and the carbonyl oxygen groups of the amino acid ester. The possible mechanism of the chiral induction process was further studied by DFT calculations. |
| |
| Keywords: | Chiral induction Porphyrin Amides Amino acids Zinc |
|
|
