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

dc.creatorSantoyo, Blanca M.
dc.creatorGonzález Romero, Carlos
dc.creatorZárate‐Zárate, Daniel
dc.creatorHernández‐Benitez, R. Israel
dc.creatorPelayo, Vanessa
dc.creatorBarrera, Edson
dc.creatorEscalante, Carlos H.
dc.creatorFuentes Benítes, Aydeé
dc.creatorMartínez‐Morales, Guadalupe
dc.creatorLópez, Julio
dc.creatorMENDOZA DELGADO, FRANCISCO JAVIER
dc.creatorVázquez Guevara, Miguel Angel
dc.creatorJiménez‐Vázquez, Hugo A.
dc.creatorTamariz, Joaquín
dc.date2019-10-31T19:25:48Z
dc.date2019-10-31T19:25:48Z
dc.date2019-07-18
dc.date.accessioned2023-07-20T13:18:17Z
dc.date.available2023-07-20T13:18:17Z
dc.identifier0899-0042
dc.identifierhttp://hdl.handle.net/20.500.11799/104772
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/7716716
dc.descriptionEn este trabajo se describe la reactividad de las oxazolidin-2-onas en un ambiente quiral obteniéndose resultados novedosos, los cuales se describen extensamente.
dc.descriptionEnantiopure 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.
dc.descriptionInstituto Politécnico Nacional, Secretaria de Investigación y Estudios Avanzados de la Universidad Autónoma del Estado de México, Universidad de Guanajuato y CONACYT.
dc.languageeng
dc.publisherWiley Online Library
dc.rightsembargoedAccess
dc.rightsembargoedAccess
dc.subjectphenylethylamine
dc.subjectoxazolidinones
dc.subjecthetero‐Diels‐ Alder reaction
dc.titleEnantiopure 4‐oxazolin‐2‐ones and 4‐methylene‐2‐oxazolidinones as chiral building blocks in a divergent asymmetric synthesis of heterocycles
dc.typeArtículo


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