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Utilice este identificador para citar o enlazar este documento: https://ria.asturias.es/RIA/handle/123456789/6721


Título: Tosylhydrazide-promoted diastereoselective Intramolecular 1,3-dipolar cycloadditions: Synthesis of tetrahydropyrrolo[3,4-c]pyrazoles
Autores: Cabal, María-Paz
Escribano, Maria
Barroso, Raquel
Palabras Claves: Tosylhydrazone
Cycloaddition
Fecha Edición: 10-Ene-2014
Resumen: A very straightforward diastereoselective synthesis of tetrahydropyrrolo[3,4-c]pyrazoles by intramolecular 1,3-dipolar cycloaddition is described. The starting materials for the synthetic route are N-Boc-protected α-amino acids, which are first transformed into N-allyl-α-amino ketones through conventional methodologies. Then, a one-pot sequence that involves formation of a tosylhydrazone from the ketone, base induced decomposition of the hydrazone, and intramolecular 1,3-dipolar cycloaddition of the diazo compound generated, gives rise to the bicyclic systems with total diastereoselectivity and high preservation of the enantiomeric purity. However, the analogous process employing α-amino aldehydes lacks stereoselectivity. DFT computational modeling has been carried out to account for the different behavior of the two types of systems.
URI: https://ria.asturias.es/RIA/handle/123456789/6721
Aparece en las Colecciones:Química
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