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Synlett 1995; 1995(4): 355-357
DOI: 10.1055/s-1995-4948
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High Pressure Mediated Intramolecular Diels-Alder Reactions of Furans with Unactivated Methylenecyclopropane Terminators

Thomas Heiner, Stephan Michalski, Kerstin Gerke, Gabriele Kuchta, Michael Buback, Armin de Meijere*
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2-6, D-37077 Göttingen, Germany
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Publikationsdatum:
31. Dezember 2000 (online)

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Furfuryl derivatives 3 with an allyl ether or allylamine type linkage to a methylenecyclopropane moiety readily undergo intramolecular Diels-Alder reactions at 10-12 kbar to yield interesting new spirocyclopropane-annelated tricyclic structures 4 diastereoselectively in excellent yields. The starting materials 3 are readily obtained by Pd0-catalysed nucleophilic allylic substitution on 1-chloro-1-ethenylcyclopropane 1 with furfurol or furfurylamine. Some acid-catalysed ring-openings of the 7’-methoxy derivative 4d are described as well. Furthermore, activation parameters for the intramolecular cycloaddition of 3a have been determined by means of on-line infrared spectroscopy under high pressure.

Diels-Alder reactions - high pressure reactions - intramolecular - methylenecyclopropanes as dienophiles - allylic substitution - Pd0-catalysed