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Title

Optically active macrocyclic hexaazapyridinophanes decorated at the periphery: synthesis and applications in the NMR enantiodiscrimination of carboxylic acids

AuthorsBusto, Eduardo; González-Álvarez, Almudena; Gotor-Fernández, Vicente; Alfonso, Ignacio ; Gotor, Vicente
KeywordsMacrocycles
Polyamines
Templated synthesis
Chiral solvating agents
NMR
Issue Date2010
PublisherElsevier
CitationTetrahedron
AbstractA family of pyridine based dialdehydes has been efficiently prepared starting from chelidamic acid by chemical modification of its 4-hydroxyl group. The condensation of these dialdehydes with commercially available (1R,2R)-(−)-cyclohexane-1,2-diamine in the presence of Ba2+ template led, after the in situ reduction, to the synthesis of a family of enantiopure hexaazapyridinophanes substituted at the periphery. These new receptors have been used as chiral shift agents towards different carboxylic acids. Good splitting of the carboxylic acid NMR signals (up to ΔΔδ=0.13 ppm) were observed using substoichiometrical amount of the receptor.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2010.06.009
URIhttp://hdl.handle.net/10261/53358
DOI10.1016/j.tet.2010.06.009,
ISSN0040-4020
Appears in Collections:(IQAC) Artículos
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