Self-assembly of achiral and chiral macrocyclic ligands: synthesis, protonation constants, conformation and asymmetric catalysis
1
Department of Chemistry, Texas A & M University, College Station, Texas 77843-3255, USA
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Publication type: Journal Article
Publication date: 2003-07-24
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
DOI:
10.1039/b303678m
PubMed ID:
12948207
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
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.
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GAO J., MARTELL A. E. Self-assembly of achiral and chiral macrocyclic ligands: synthesis, protonation constants, conformation and asymmetric catalysis // Organic and Biomolecular Chemistry. 2003. Vol. 1. No. 15. p. 2795.
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GAO J., MARTELL A. E. Self-assembly of achiral and chiral macrocyclic ligands: synthesis, protonation constants, conformation and asymmetric catalysis // Organic and Biomolecular Chemistry. 2003. Vol. 1. No. 15. p. 2795.
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TY - JOUR
DO - 10.1039/b303678m
UR - https://doi.org/10.1039/b303678m
TI - Self-assembly of achiral and chiral macrocyclic ligands: synthesis, protonation constants, conformation and asymmetric catalysis
T2 - Organic and Biomolecular Chemistry
AU - GAO, Jian
AU - MARTELL, ARTHUR E.
PY - 2003
DA - 2003/07/24
PB - Royal Society of Chemistry (RSC)
SP - 2795
IS - 15
VL - 1
PMID - 12948207
SN - 1477-0520
SN - 1477-0539
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2003_GAO,
author = {Jian GAO and ARTHUR E. MARTELL},
title = {Self-assembly of achiral and chiral macrocyclic ligands: synthesis, protonation constants, conformation and asymmetric catalysis},
journal = {Organic and Biomolecular Chemistry},
year = {2003},
volume = {1},
publisher = {Royal Society of Chemistry (RSC)},
month = {jul},
url = {https://doi.org/10.1039/b303678m},
number = {15},
pages = {2795},
doi = {10.1039/b303678m}
}
Cite this
MLA
Copy
GAO, Jian, and ARTHUR E. MARTELL. “Self-assembly of achiral and chiral macrocyclic ligands: synthesis, protonation constants, conformation and asymmetric catalysis.” Organic and Biomolecular Chemistry, vol. 1, no. 15, Jul. 2003, p. 2795. https://doi.org/10.1039/b303678m.