Chiral macrocyclic aliphatic oligoimines derived from trans-1,2-diaminocyclohexane
2007 | journal article. A publication with affiliation to the University of Göttingen.
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Chiral macrocyclic aliphatic oligoimines derived from trans-1,2-diaminocyclohexane
Kwit, M.; Plutecka, A.; Rychlewska, U.; Gawronski, J.; Khlebnikov, A. F.; Kozhushkov, S. I. & Rauch, K. et al. (2007)
Chemistry - A European Journal, 13(31) pp. 8688-8695. DOI: https://doi.org/10.1002/chem.200700648
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- Authors
- Kwit, Marcin; Plutecka, Agnieszka; Rychlewska, Urszula; Gawronski, Jacek; Khlebnikov, Alexander F.; Kozhushkov, Sergei I.; Rauch, Karsten; Meijere, Armin de
- Abstract
- Aliphatic dialdehydes of rigid structures having a cyclohexane, a bicyclo[2.2.2]octane or a [7]triangulane skeleton, have been condensed with enantiomerically pure trans- 1,2-diami-nocyclohexane to give [3+3] or [2+2] macrocyclization products. Unlike acyclic aliphatic imines, these macrocyclic oligomines show enhanced stabilities and their structures in the crystals could be determined by X-ray diffraction analyses. The enantiomerically pure [7]triangulane dialdehyde showed remarkable diastereoselectivity in the condensation with the two enantiomers of trans-1,2-diaminocyclohexane: only one of the enantiomers gave a [2+2] macrocyclization product. Circular dichroism measurements combined with computational analysis show that the lowest energy electronic transition in these cyclic oligomines is of n-pi type.
- Issue Date
- 2007
- Journal
- Chemistry - A European Journal
- ISSN
- 0947-6539