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

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

Chemistry (Weinheim an der Bergstrasse, Germany) (2007-07-31)
Marcin Kwit, Agnieszka Plutecka, Urszula Rychlewska, Jacek Gawroński, Alexander F Khlebnikov, Sergei I Kozhushkov, Karsten Rauch, Armin de Meijere
摘要

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-pi* type.

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Sigma-Aldrich
(±)-反式-1,2-二氨基环己烷, 99%