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Issue 15, 2003
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Self-assembly of achiral and chiral macrocyclic ligands: synthesis, protonation constants, conformation and asymmetric catalysis

Jian Gaoa  and  Arthur E. Martell*a 
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* Corresponding authors

a Department of Chemistry, Texas A & M University, College Station, USA

Abstract

New 30-membered achiral and chiral polyaza macrocyclic ligands, L1 and L2 were synthesized directly from [3 + 3] condensation of phthalic dicarboxaldehyde with cis- and (1R,2R)-diaminocyclohexane, respectively. The trimeric macrocyclic structures were confirmed by electrospray ionization mass spectrometry (ESI-MS), 1H NMR, 13C NMR spectroscopy and elemental analysis. Potentiometry was used to determine the protonation constants of the ligands. UV–vis spectrophotometric titration was employed to investigate the coordination and conformational properties of the chiral ligand (L2). Direct enantioselective aldol reaction has been successfully performed using 4-nitrobenzaldehyde and acetone in the presence of the chiral macrocycle and its zinc(II) complexes as catalysts.

Graphical abstract: Self-assembly of achiral and chiral macrocyclic ligands: synthesis, protonation constants, conformation and asymmetric catalysis

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Publication details

The article was received on 02 Apr 2003, accepted on 04 Jun 2003 and first published on 02 Jul 2003


Article type: Paper
DOI: 10.1039/B303678M
Citation: Org. Biomol. Chem., 2003,1, 2795-2800
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    Self-assembly of achiral and chiral macrocyclic ligands: synthesis, protonation constants, conformation and asymmetric catalysis

    J. Gao and A. E. Martell, Org. Biomol. Chem., 2003, 1, 2795
    DOI: 10.1039/B303678M

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