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Chiral macrocyclic aliphatic oligoimines derived from trans-1,2- diaminocyclohexane. / Kwit, Marcin; Plutecka, Agnieszka; Rychlewska, Urszula; Gawroński, Jacek; Khlebnikov, Alexander F.; Kozhushkov, Sergei I.; Rauch, Karsten; De Meijere, Armin.

In: Chemistry - A European Journal, Vol. 13, No. 31, 08.11.2007, p. 8688-8695.

Research output: Contribution to journal › Article › peer-review

Harvard

Kwit, M, Plutecka, A, Rychlewska, U, Gawroński, J, Khlebnikov, AF, Kozhushkov, SI, Rauch, K & De Meijere, A 2007, 'Chiral macrocyclic aliphatic oligoimines derived from trans-1,2- diaminocyclohexane', Chemistry - A European Journal, vol. 13, no. 31, pp. 8688-8695. https://doi.org/10.1002/chem.200700648

APA

Kwit, M., Plutecka, A., Rychlewska, U., Gawroński, J., Khlebnikov, A. F., Kozhushkov, S. I., Rauch, K., & De Meijere, A. (2007). Chiral macrocyclic aliphatic oligoimines derived from trans-1,2- diaminocyclohexane. Chemistry - A European Journal, 13(31), 8688-8695. https://doi.org/10.1002/chem.200700648

Vancouver

Kwit M, Plutecka A, Rychlewska U, Gawroński J, Khlebnikov AF, Kozhushkov SI et al. Chiral macrocyclic aliphatic oligoimines derived from trans-1,2- diaminocyclohexane. Chemistry - A European Journal. 2007 Nov 8;13(31):8688-8695. https://doi.org/10.1002/chem.200700648

Author

Kwit, Marcin ; Plutecka, Agnieszka ; Rychlewska, Urszula ; Gawroński, Jacek ; Khlebnikov, Alexander F. ; Kozhushkov, Sergei I. ; Rauch, Karsten ; De Meijere, Armin. / Chiral macrocyclic aliphatic oligoimines derived from trans-1,2- diaminocyclohexane. In: Chemistry - A European Journal. 2007 ; Vol. 13, No. 31. pp. 8688-8695.

BibTeX

@article{c8ee0daf8708464dbdd4386cd398888d,
title = "Chiral macrocyclic aliphatic oligoimines derived from trans-1,2- diaminocyclohexane",
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-diaminocyclohexane to give [3 + 3] or [2 + 2] macrocyclization products. Unlike acyclic aliphatic imines, these macrocyclic oligoimines 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 oligoimines is of n-π* type.",
keywords = "Circular dichroism, Diastereoselectivity, Imines, Triangulanes, X-ray diffraction",
author = "Marcin Kwit and Agnieszka Plutecka and Urszula Rychlewska and Jacek Gawro{\'n}ski and Khlebnikov, {Alexander F.} and Kozhushkov, {Sergei I.} and Karsten Rauch and {De Meijere}, Armin",
year = "2007",
month = nov,
day = "8",
doi = "10.1002/chem.200700648",
language = "English",
volume = "13",
pages = "8688--8695",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-Blackwell",
number = "31",

}

RIS

TY - JOUR

T1 - Chiral macrocyclic aliphatic oligoimines derived from trans-1,2- diaminocyclohexane

AU - Kwit, Marcin

AU - Plutecka, Agnieszka

AU - Rychlewska, Urszula

AU - Gawroński, Jacek

AU - Khlebnikov, Alexander F.

AU - Kozhushkov, Sergei I.

AU - Rauch, Karsten

AU - De Meijere, Armin

PY - 2007/11/8

Y1 - 2007/11/8

N2 - 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-diaminocyclohexane to give [3 + 3] or [2 + 2] macrocyclization products. Unlike acyclic aliphatic imines, these macrocyclic oligoimines 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 oligoimines is of n-π* type.

AB - 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-diaminocyclohexane to give [3 + 3] or [2 + 2] macrocyclization products. Unlike acyclic aliphatic imines, these macrocyclic oligoimines 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 oligoimines is of n-π* type.

KW - Circular dichroism

KW - Diastereoselectivity

KW - Imines

KW - Triangulanes

KW - X-ray diffraction

UR - http://www.scopus.com/inward/record.url?scp=35748980025&partnerID=8YFLogxK

U2 - 10.1002/chem.200700648

DO - 10.1002/chem.200700648

M3 - Article

C2 - 17661323

AN - SCOPUS:35748980025

VL - 13

SP - 8688

EP - 8695

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 31

ER -

ID: 28188479