期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 13, 期 31, 页码 8688-8695出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200700648
关键词
circular dichroism; diastereoselectivity; imines; triangulanes; X-ray diffraction
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.
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