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

被引：38

作者：

Gao, J ^{[1
]}

Martell, AE ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2003年 / 1卷 / 15期

关键词：

D O I：

10.1039/b303678m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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), H-1 NMR, C-13 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.

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页码：2795 / 2800

页数：6

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