Enantiopure polyfunctionalized imidazo[1,2-a]pyridines and pyrrolo[1,2-a]imidazoles, two classes of heterocyclic compounds including anti-inflammatories and glycosidase inhibitors, were synthesized starting from natural α-aminoacids and exploiting an intramolecular nitrone cycloaddition as the key step. The regiochemistry of the cycloaddition, which determines the product distribution, was markedly dependent on the R substituent and, therefore, submitted to a theoretical study by means of ab initio and MP2 calculations.

Intramolecular cycloadditions of nitrones derived from optically active 1-alkenyl-2-imidazolecarbaldehydes: regio- and diastereoselectivity / E.M. Beccalli, G. Broggini, A. Contini, I. De Marchi, G. Zecchi, C. Zoni. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 15:20(2004), pp. 3181-3187. [10.1016/j.tetasy.2004.07.065]

Intramolecular cycloadditions of nitrones derived from optically active 1-alkenyl-2-imidazolecarbaldehydes: regio- and diastereoselectivity

E.M. Beccalli
Primo
;
A. Contini;C. Zoni
Ultimo
2004

Abstract

Enantiopure polyfunctionalized imidazo[1,2-a]pyridines and pyrrolo[1,2-a]imidazoles, two classes of heterocyclic compounds including anti-inflammatories and glycosidase inhibitors, were synthesized starting from natural α-aminoacids and exploiting an intramolecular nitrone cycloaddition as the key step. The regiochemistry of the cycloaddition, which determines the product distribution, was markedly dependent on the R substituent and, therefore, submitted to a theoretical study by means of ab initio and MP2 calculations.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/145364
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