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A new approach to enantiomerically pure bis-imidazoles derived from trans-1,2-diaminocyclohexane


Mucha, P; Mloston, G; Jasinski, M; Linden, A; Heimgartner, H (2008). A new approach to enantiomerically pure bis-imidazoles derived from trans-1,2-diaminocyclohexane. Tetrahedron: Asymmetry, 19 (13):1600-1607.

Abstract

Racemic as well as enantiomerically pure trans-1,10-(cyclohexane-1,2-diyl)bis(imidazole N-oxides) were prepared from trans-cyclohexane-1,2-bis(methylidenamine) and 1,2-dione monooximes (a-hydroxyiminoketones).
The enantiomeric purity of selected products was determined by means of 1H NMR spectroscopy in the presence of (+)-(R)-(tert butyl)(phenyl)phosphonothioic acid as a chiral solvating agent. Deoxygenation by treatment with Raney-nickel led to the corresponding chiral bis-imidazoles.

Abstract

Racemic as well as enantiomerically pure trans-1,10-(cyclohexane-1,2-diyl)bis(imidazole N-oxides) were prepared from trans-cyclohexane-1,2-bis(methylidenamine) and 1,2-dione monooximes (a-hydroxyiminoketones).
The enantiomeric purity of selected products was determined by means of 1H NMR spectroscopy in the presence of (+)-(R)-(tert butyl)(phenyl)phosphonothioic acid as a chiral solvating agent. Deoxygenation by treatment with Raney-nickel led to the corresponding chiral bis-imidazoles.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:July 2008
Deposited On:06 Feb 2009 13:30
Last Modified:05 Apr 2016 12:57
Publisher:Elsevier
ISSN:0957-4166
Funders:Polish Ministry for Science and Higher Education, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1016/j.tetasy.2008.06.015

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