TY - JOUR
T1 - Synthesis of exo-Imidazolidin-2-one Dienes, Their Isomerization, and Selectivity in Diels-Alder Cycloadditions
AU - Espinoza-Hicks, Carlos
AU - Montoya, Pablo
AU - Bautista, Rafael
AU - Jiménez-Vázquez, Hugo A.
AU - Rodríguez-Valdez, Luz M.
AU - Camacho-Dávila, Alejandro A.
AU - Cossío, Fernando P.
AU - Delgado, Francisco
AU - Tamariz, Joaquín
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/5/18
Y1 - 2018/5/18
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85047258152&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b02344
DO - 10.1021/acs.joc.7b02344
M3 - Artículo
C2 - 29697257
SN - 0022-3263
VL - 83
SP - 5347
EP - 5364
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 10
ER -