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Synlett 1998; 1998(2): 159-160
DOI: 10.1055/s-1998-1593
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Intramolecular Diels-Alder Reaction with an α-Methylene Lactone as Dienophile

Martin E. Maier* , Caroline Perez
  • *Martin-Luther-Universität Halle-Wittenberg, Fachbereich Chemie, Institut für Organische Chemie, Kurt-Mothes-Str. 2, 06120 Halle (Saale), Germany; Fax (+49) 345 55 270 30; E-mail: maier@chemie.uni-halle.de
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Publikationsdatum:
31. Dezember 2000 (online)

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Starting from the alcohol 1, the α-methylene-γ-butyrolactone 4 was prepared. This triene underwent an intramolecular Diels-Alder reaction at 110 °C to give the tricyclic cycloadducts 5 a, b in 74% yield. The thermal reaction produced mainly the endo-isomer 5 a (endo/exo = 6 : 1).

intramolecular Diels-Alder - decaline system - force-field calculations