2024-03-28T09:14:40Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/533582020-07-03T13:04:38Zcom_10261_5063com_10261_5col_10261_5066
http://hdl.handle.net/10261/53358
10.1016/j.tet.2010.06.009,
55263
Optically active macrocyclic hexaazapyridinophanes decorated at the periphery: synthesis and applications in the NMR enantiodiscrimination of carboxylic acids
Elsevier
2010
artículo
Busto, Eduardo
González-Álvarez, Almudena
Gotor-Fernández, Vicente
Alfonso, Ignacio
rp13740
Gotor, Vicente
Macrocycles
Polyamines
Templated synthesis
Chiral solvating agents
NMR
2010
A 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.
Tetrahedron