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Chiral Macrocyclic Aliphatic Oligoimines Derived from trans ‐1,2‐Diaminocyclohexane
Author(s) -
Kwit Marcin,
Plutecka Agnieszka,
Rychlewska Urszula,
Gawroński Jacek,
Khlebnikov Alexander F.,
Kozhushkov Sergei I.,
Rauch Karsten,
de Meijere Armin
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700648
Subject(s) - enantiomer , chemistry , circular dichroism , octane , cyclohexane , condensation , stereochemistry , bicyclic molecule , crystallography , organic chemistry , physics , thermodynamics
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.