Why a proximity-induced Diels-Alder reaction is so fast |
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| Authors: | Krenske Elizabeth H Perry Emma W Jerome Steven V Maimone Thomas J Baran Phil S Houk K N |
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| 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 |
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| 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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