Designing large triangular chiral macrocycles: efficient
Publication type: Journal Article
Publication date: 2000-08-17
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
10970322
Organic Chemistry
Abstract
Triangular 30- and 27-membered hexaiminomacrocycles 4 and 5 of D(3) and C(3) symmetry, respectively, are readily obtained by unprecedented [3 + 3] cyclocondensation of (R,R)-1, 2-diaminocyclohexane with, accordingly, terephthalaldehyde and isophthalaldehyde. The course of the reaction, leading to macrocyclization, is governed by conformational constraints imposed on the structural components of the intermediate products, as shown by molecular modeling. X-ray analysis of cocrystal 4.AcOEt revealed that the macrocycle symmetry significantly departs from ideal D(3) symmetry due to crystal environment. Cyclic hexaamines 6 and 7 were prepared by sodium borohydride reduction of 4 and 5, respectively.
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Metrics
162
Total citations:
162
Citations from 2025:
5
(3.09%)
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GOST
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Gawroński J. et al. Designing large triangular chiral macrocycles: efficient // Journal of Organic Chemistry. 2000. Vol. 65. No. 18. pp. 5768-5773.
GOST all authors (up to 50)
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Gawroński J., Kołbon H., Kwit M., Katrusiak A. Designing large triangular chiral macrocycles: efficient // Journal of Organic Chemistry. 2000. Vol. 65. No. 18. pp. 5768-5773.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo000623v
UR - https://doi.org/10.1021/jo000623v
TI - Designing large triangular chiral macrocycles: efficient
T2 - Journal of Organic Chemistry
AU - Gawroński, J.
AU - Kołbon, H
AU - Kwit, M
AU - Katrusiak, Andrzej
PY - 2000
DA - 2000/08/17
PB - American Chemical Society (ACS)
SP - 5768-5773
IS - 18
VL - 65
PMID - 10970322
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2000_Gawroński,
author = {J. Gawroński and H Kołbon and M Kwit and Andrzej Katrusiak},
title = {Designing large triangular chiral macrocycles: efficient},
journal = {Journal of Organic Chemistry},
year = {2000},
volume = {65},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/jo000623v},
number = {18},
pages = {5768--5773},
doi = {10.1021/jo000623v}
}
Cite this
MLA
Copy
Gawroński, J., et al. “Designing large triangular chiral macrocycles: efficient.” Journal of Organic Chemistry, vol. 65, no. 18, Aug. 2000, pp. 5768-5773. https://doi.org/10.1021/jo000623v.