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

Autor:	Alessandro Contini, Gaetano Zecchi, Egle M. Beccalli, Ivan De Marchi, Caterina Zoni, Gianluigi Broggini
Rok vydání:	2004
Předmět:	chemistry.chemical_classification Stereochemistry Organic Chemistry Ab initio Substituent Regioselectivity Catalysis Product distribution Cycloaddition Nitrone Inorganic Chemistry chemistry.chemical_compound Enantiopure drug chemistry Intramolecular force Physical and Theoretical Chemistry
Zdroj:	Tetrahedron: Asymmetry. 15:3181-3187
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2004.07.065
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::5ff2bf6e2a0f92b2748417e03dd8579e https://doi.org/10.1016/j.tetasy.2004.07.065 Zobrazit plný text záznamu Full Text from ScienceDirect