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Why a proximity-induced Diels-Alder reaction is so fast
Authors:Krenske Elizabeth H  Perry Emma W  Jerome Steven V  Maimone Thomas J  Baran Phil S  Houk K N
Institution:School of Chemistry, University of Melbourne, and Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology, VIC 3010, Australia. ekrenske@unimelb.edu.au
Abstract:Unlike normal Diels-Alder reactions of acyclic alkadienes with alkenes, the vinylbicyclo2.2.2]octene employed in the Baran total synthesis of vinigrol undergoes a quantitative Diels-Alder reaction with a tethered alkene at room temperature. Density functional theory calculations reveal that this unprecedented reactivity originates from a combination of preorganization, diene strain, and tether stabilization.
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