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Chiral recognition of amino acid esters by a novel oxalic amide-linked bisporphyrin†
Jiaxun Jiang,Zhiqiang Feng,Baozhen Liu,Yong Wang
Dalton Transactions Pub Date : 03/06/2013 00:00:00 , DOI:10.1039/C3DT50380A
Abstract

A novel oxalic amide-linked bisporphyrinate 1 has been designed and synthesized, which shows chiral recognition ability for amino acid ethyl esters. The structure of complex 1·(D-Phe-OEt)(L-Phe-OEt) has been solved by X-ray crystallography. It reveals the following information: bisporphyrin unit adopts anti-configuration; compound 1 forms 1 : 2 complex with amino acid ethyl esters; one important hydrogen bond is formed between the coordinated nitrogen of amino acid ester and carbonyl oxygen in the amide group. The chiral recognition mechanism has been further investigated by UV-Vis spectra, 1H NMR and DFT/TDDFT calculations.

Graphical abstract: Chiral recognition of amino acid esters by a novel oxalic amide-linked bisporphyrin
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