The Hantzsch reaction of C-glycosyl aldehyde/enamino ester/beta-ketoester systems under L-proline catalysis to give dihydropyridine C-glycoconjugates is reported. Asymmetric cyclocondensations of differentially substituted enamine and beta-dicarbonyl components with formyl alpha-L-C-threofuranoside and with the alpha-D-isomer were also carried out. Each reaction occurred with high yet opposite stereoselectivity (de >95%) so that the pair of alpha-threofuranose C-nucleoside enantiomers was prepared.

Dihydropyridine C-glycoconjugates by organocatalytic Hantzsch cyclocondensation. Stereoselective synthesis of alpha-threofuranose C-nucleoside enantiomers

MASSI, Alessandro;DONDONI, Alessandro
2009

Abstract

The Hantzsch reaction of C-glycosyl aldehyde/enamino ester/beta-ketoester systems under L-proline catalysis to give dihydropyridine C-glycoconjugates is reported. Asymmetric cyclocondensations of differentially substituted enamine and beta-dicarbonyl components with formyl alpha-L-C-threofuranoside and with the alpha-D-isomer were also carried out. Each reaction occurred with high yet opposite stereoselectivity (de >95%) so that the pair of alpha-threofuranose C-nucleoside enantiomers was prepared.
2009
Ducatti, D. R. B.; Massi, Alessandro; Noseda, M. D.; Duarte, M. E. R.; Dondoni, Alessandro
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/1378492
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