Hetero-Diels-Alder reaction of phosphinyl and phosphonyl nitroso alkenes with conjugated dienes: an aza-Cope rearrangement |
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Authors: | de los Santos Jesús M Ignacio Roberto Rubiales Gloria Aparicio Domitila Palacios Francisco |
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Affiliation: | Departamento de Química Orgánica I, Facultad de Farmacia, Centro de Investigaciones y Estudios Avanzados Lucio Lascaray, Universidad del País Vasco, Apartado 450, 01080 Vitoria, Spain. |
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Abstract: | Phosphorylated nitroso alkenes react with cyclic dienes such as cyclopentadiene or cyclohexadiene to afford hetero Diels-Alder-type cycloadducts where the nitroso alkene participates as dienophile component and the cyclic olefin acts as the 4π-electron (diene) system. Subsequent aza-Cope rearrangement affords highly functionalized 5,6-dihydro-4H-1,2-oxazines. Conversely, the reaction of TMS-substituted cyclopentadiene (dienophile) with nitroso alkenes as heterodienes leads directly to bicyclic 1,2-oxazines. Theoretical studies are in agreement with the experimental results and with the new aza-Cope rearrangement proposed. |
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