Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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.
в: Chemistry - A European Journal, Том 13, № 31, 08.11.2007, стр. 8688-8695.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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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