Issue 21, 2013
From the journal:

Dalton Transactions

Chiral recognition of amino acid esters by a novel oxalic amide-linked bisporphyrin†

Jiaxun Jiang,a   Zhiqiang Feng,a   Baozhen Liu,a   Chuanjiang Hu*ab  and  Yong Wang*a  

* Corresponding authors

a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China
E-mail: cjhu@suda.edu.cn
Fax: +86-25-65880903
Tel: +86-25-65880903

b State Key Laboratory and Coordination Chemistry Institute, Nanjing University, Nanjing 210093, P. R. China

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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Article information

DOI
https://doi.org/10.1039/C3DT50380A
Article type
Paper
Submitted
07 Feb 2013
Accepted
06 Mar 2013
First published
06 Mar 2013

Dalton Trans., 2013,42, 7651-7659

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

J. Jiang, Z. Feng, B. Liu, C. Hu and Y. Wang, Dalton Trans., 2013, 42, 7651 DOI: 10.1039/C3DT50380A

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