Enantiopure 4-oxazolin-2-ones and 4-methylene-2-oxazolidinones as chiral building blocks in a divergent asymmetric synthesis of heterocycles

Blanca M. Santoyo, Carlos González-Romero, Daniel Zárate-Zárate, R. Israel Hernández-Benitez, Vanessa Pelayo, Edson Barrera, Carlos H. Escalante, Aydeé Fuentes-Benites, Guadalupe Martínez-Morales, Julio López, Miguel A. Vázquez, Francisco Delgado, Hugo A. Jiménez-Vázquez, Joaquín Tamariz

Producción científica: Contribución a una revistaArtículorevisión exhaustiva

5 Citas (Scopus)

Resumen

Enantiopure 3-((R)- and 3-((S)-1-phenylethyl)-4-oxazoline-2-ones were evaluated as chiral building blocks for the divergent construction of heterocycles with stereogenic quaternary centers. The N-(R)- or N-(S)-1-phenylethyl group of these compounds proved to be an efficient chiral auxiliary for the asymmetric induction of the 4- and 5-positions of the 4-oxazolin-2-one ring through thermal and MW-promoted nucleophilic conjugated addition to Michael acceptors and alkyl halides. The resulting adducts were transformed via a cascade process into fused six-membered carbo- and heterocycles. The structure of the reaction products depended on the electrophiles and reaction conditions used. Alternative isomeric 4-methylene-2-oxazolidinones served as chiral precursors for a versatile and divergent approach to highly substituted cyclic carbamates. DFT quantum calculations showed that the formation of bicyclic pyranyl compounds was generated by a diastereoselective concerted hetero-Diels-Alder cycloaddition.

Idioma originalInglés
Páginas (desde-hasta)719-749
Número de páginas31
PublicaciónChirality
Volumen31
N.º9
DOI
EstadoPublicada - sep. 2019

Huella

Profundice en los temas de investigación de 'Enantiopure 4-oxazolin-2-ones and 4-methylene-2-oxazolidinones as chiral building blocks in a divergent asymmetric synthesis of heterocycles'. En conjunto forman una huella única.

Citar esto