Synthesis of exo-Imidazolidin-2-one Dienes, Their Isomerization, and Selectivity in Diels-Alder Cycloadditions

Carlos Espinoza-Hicks, Pablo Montoya, Rafael Bautista, Hugo A. Jiménez-Vázquez, Luz M. Rodríguez-Valdez, Alejandro A. Camacho-Dávila, Fernando P. Cossío, Francisco Delgado, Joaquín Tamariz

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Abstract

An efficient and alternative synthesis of exo-imidazolidin-2-one dienes is described. A condensation reaction was carried out with bis-imino derivatives, diacetyl, and triphosgene, affording symmetrically N,N-disubstituted dienes. The use of alkyl methyl α-diketones led to the formation of nonsymmetrical dienes, which underwent isomerization to provide more stable inner-outer-ring dienes under Lewis acid conditions. Evaluation was made of the reactivity as well as regio- and stereoselectivity of these dienes in Diels-Alder reactions. They proved to be highly reactive and selective. DFT calculations of the transition states accounted for their behavior.

Original languageEnglish
Pages (from-to)5347-5364
Number of pages18
JournalJournal of Organic Chemistry
Volume83
Issue number10
DOIs
StatePublished - 18 May 2018

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