Why a proximity-induced Diels-Alder reaction is so fast.

نویسندگان

  • Elizabeth H Krenske
  • Emma W Perry
  • Steven V Jerome
  • Thomas J Maimone
  • Phil S Baran
  • K N Houk
چکیده

Unlike normal Diels-Alder reactions of acyclic alkadienes with alkenes, the vinylbicyclo[2.2.2]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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عنوان ژورنال:
  • Organic letters

دوره 14 12  شماره 

صفحات  -

تاریخ انتشار 2012